SCIENTIFIC ABSTRACT RUBTSOV, L.N. - RUBTSOV, M.V.

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• Collection: Scientific Abstracts
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• Document Creation Date: November 2, 2016
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• Sequence Number: 1
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

- ----- ----
-57471-65
L
Acawmff mi: AR5ol6WI
nt~
J
year. A studLy ww meA of the behavior of the sporadle 3 and Be Imyers and of
their relationship to meteoric activity. In smardance witil tile AAersdn"

RUBTSOV, L.N.
Preliminary results of it vertical sounding of the ionosphere
above Tadzhikistan. Biul. Inst. astrcfiz. AN Tadzh. SSR no.33:
3-11 162. (MIRA 17:11)

VOLOVCHENKO., I.; METELEV, V.; BANNIKOV, N.; LAPIDUS, M.; MOROZOV, P.;
RUBTSOV M - BATSANOV,1 N.; PRYANISHNIKOV, D.N., akademik;
Fu ~Ytv ~' I akademik; BEREZIN I.A., red.; AVDMVA,
.1 N-m-1
V.A., tekhn. red.
(Strong crops] Moguchie kulltury. Moskva, Sovetskaia Rossi4,
1962. 222 p. (Truzhenikam sela - ob intensivnoi sisteme
zemledeliia, no.2) (MIRA 16:9)
(Field crops)

HIKITSXAYA, Ye.S.; RUBTS( X, M. (I .
Hydrogenation of 4-(~ cPxbetho.7QrTinvl)-pvridIne in the presence
of the nickel-skeleton catalyst. Zhur.ob.khim.26 n6.110119~3M N156.
(M1RA 10:1)
1. VseRovu%ny nauchno.4ssledovatel'skiy khimiko-fnrmRtsevticheskly
institut imi;ij S.Ordzhonikidze.
(Pyridine) (Hydrogenation)

/OjX6U3bW/W3/Q01/"4-

AU"ORS Carif I mav 5.
YA S., OwWifat* of ftaics and N~Ib"Mtlovp,
vubtfave, no Jop 1%yolatott Bysh"now I, To. K., phystales
p .*r. spectra In. ailicate Slastom containing %braw-valout
t1tanim
PE310DICALs Staklo i kormOkil, noa 30 .1961~ M-U
TIM The of most4f leato'glasses
T102 were t aken at 9320 and 450
4p ma/o"
otret,
6
A.
0
glage
T102
K factor 3
7r% too
K.77
30

0

U-519 to
W-519 15 71. It
40 t*9

Card

/07 3/001/~W
3 ragooloo
f stot to
E.par. apectrajn ei I I ca t -91 rlaoses
It wail found In an' enrl Ier Isaper (ZhUTPO 1960, V.39) khA suporabolea
solutions of TO* compotanciri have similar *.p.rs spectra. It to
therefore ooncluded thtit Wien the Clasa in selted., the TiO to partially
re4uced to T1 in M -5t7(M-519) glass the oetabe'dral aryst I tiol
f ofned' by six oxyCen atown, oplito the five-told orbital lev*,O
1 or VI
into an upper doublet and oJower triplet. The low-symnstry fields pwv.
duced by 419torti6no' of the DxyGen. octakeften sail Uy parl1oloo of A%*.
sphere of -coordinates, split tb* orbital triplet Into a lower
singlet and 46txblet~ State tbe-fiarrow e*y6*r. Jim ft*X-5tq III&w
containing 15% TiO2 is'obsirved even- al reoia. tewpereWr*v the Valais a
of,,tht splitting of -the,orbital met Im ratber~ h4A* 11h
resonance Alme it 450 - Ak/aec In glauses Ooitpinil* and M list
Is'otawr this
..Ted DOY at 7.7 *K- ~ This to explain"' 1W the toot that IN
3+ ;. .. I '
Give the 71 tone are in a Rymmetrio fivld sad the *.,per, line bosoms
~so vide'at room temperature that it cannot to observed aW aime. %a
~atrong broadening of the line at 9320 No/age to explain" by ib*
presence of two local fla'ldo.~'Thln came** a eap*rpositiong Usft% to
card 2/3

PAVLOV, Ivan Petrovich, prof. Prinimli uchastiye: TATARINTSEV, A.S.p
prof.; VIDDIIN, K.F., dots.; RUBTSM, M.I., dots.,- YERMILDVA,
A.A... dots.; RIKOVA, M.G., Y6d
[Breeding and seed production of vegetable crops) Selektaiia i
semenovodstvo ovoshchnykh,kulltur. Moskval.Seltkhozizdat
1963. 279 pe (NIRA 17:1'1)
1. Plodoovashchnyy institut im. I.V.Michurina (for Tatarintsev,'
Videnin, Rubtsov, Yermilova).

RUBTSOV, id
L.L_dgts.; YEfIMILOVA, A.A., dots.; CHEREPOVA, 0 M. kar
sellkhoz.nauk; SKMPNIKOV, Yu.G.., dots.; DOROKHOV, A.A., kand.
sellkhoz.nauk; LITVINOVA, M.K., assistent; MUSTAFIN, A.M., pre-
podavatelf; PESHKOV, V.P., red.; POPOV, V.N., tekhn. red.
[Growing vegetables in the Central Chernozem Region of the
U.S.S.R.]Vyrashchivanie ovoshchei v TSentrallnoi chernozemnoi
zone SSSR. Tambov, Tambovskoe knizhnoe izd-vo, 1962. 110 p.
(miRA 16:2)
1. Sotrudnikikafedry ovoshchevodstva Michurinskogo plodoovoshch-
nogo instituta im.I.V.Michurina (for all except Peshkov, Popov).
(Central Chernozem-Region-Vegetable gardening)

tax
IIF~mdanentals of the Gm-ring of Seedling Tomatoes in Sheltered Ground Harmed 'by
Steavi.11 Cand Agr Sci, 1-11oscovi Order of Lenin Agricultural Acad imeni K. A. T3*nlryazev,
Moscow, 1955. (KL, No 16, Apr 55)
SO: Sira. No. 704, 2 Nov 55 Survey of Scientific and Technical Dissex-t ations Defended
at USSR Higher Educational Institutions.(16).

RUBTSOT,,A.K_; YELIASHVILI, A.I., inzh.; PASHCBXUKO, I.N., insh.;
YAKUNIN, V.I.-, inzh.; MMUMOV, Y6.K., inzh., obahchiy red.;
GOLUBEVA, I.A., red.; USHKOVA, M., takhn.rod.
[Simplest mettiods for making bricks] Prosteishie sposoby
izgotovleniiakirp~cha. Koakva; 1958. 69 p. JKIRA 12:8).
1. Russia (1923- U.S.S.R.) Kinisterstvo sel'skogo khozyaystva.
Upravleniye kapitallnogo stroitellstva.
Orickmaking)

(Rural electrification)

USSR Farm Animals. cattle Q-2
Abs.Jour: Ref Zhur-Biol., No 3, 1958, 12067
Author Rubtsov M. K.
Inst
'Title On the Composition of Feed Rations for Pregnant Dry
Cows (0 6trukture kormovykh ratsionov dla stel!nykh
sukhostoynykh korov)
Orig Pub: Sovkoznoye proiz-vo, 1957, No 5, 49-54
Abstract: An experiment was carried.out on five groups.of the
pregnant-dry Cows of the East Friesian breed. The
beetroot-silage group was fed rations containing
16.6 kg. of beetroot and 8.8 kg. of silage; the sil-
age group - 16.6 kg. of silage; the beetroot group
25 kg. of beetroot; the potato group - 10.5 kg.
of potatoes; the "dryration" group.- 12 kg.,of beet-
root. All group rations included 11.6 to 12 kg. cf,
Card 1/2

V~Sl Animals. Cattle Q-2
Abs Jour: Ref Zhur-Biol., No 3, 1958, 12o67
'Abstract: hay each, and 2.5 to 4.6 kg. of concentrates. As
a result of the experiment the live weight of com.
during dry period increaseA in,all five groups by
51-41-42-56-53.7 kg. respectively; .on the 3 1 5thI day
after calving it,decreased by 77-~89-87-74-70 kg.;'
the Hb of the blood, during 1st month od.fry period
increased by 4-3-3-0-5%; the milk yield~for the 60
days of lactation was 1,457-1,257,1,317_1,574-1,360~
kg., and for 300 days constituted 5,317-.4,936-5,092-
5,915-4,848 kg,., respectively. On the basis of the
data pro Ivided by the experiments the conclusion was
drawn that succulent rations were advantageous in
the preparation of the cows for calving. The beet-
root-silage ration was, the best.
Card 2/2

S.MCHENKO, A.S.; KAVUN, P.X., red,.;RUBTSOV, M.K., red.; PROKOF3YEVA, L.N...

NIKITSKAYA, Ye.S.; LEVKOYEVAJ, Ye.I.; USOVSKAYA, V.S.; RUBTSOV, M.V.
Synthesis of 7-hydroxy-9-methYl-3,9-dia2ableyelo [3,3p1) nonane
and some of its derivatives. Zhur. org. khtm.~l no,lil74-182 Ja
165. (MIRA 18:5)
y naiichno-issledovatellskiy khimiko-farm tsevticheski
1. Vsesoyuznr y institut
imeni S.Ordzhonikidze.

MIKELIANA, Ye.Ye.; VOROWMA, V-Ya.; SHEDCUMOY V.I.; RUBTSOV, M.V.
St.-dcture of 3-quinuelidinone rearrangement products.according
to the Schmidt and Beelmann reactions. Zhur. org. khim. I
no.7:1336-1337 il 165. (MIRA 181:11)
1. Vsesoy-uznyy nauchno-issledovatellskiy khimiko-farmatsevticheskiy
institut imeni S.Ordzhonikidze i Institut khimli prirodnyk-h
soyedinaniy All SSSR.

50)
AUTHORS: Mikhtlina, Ye. Ye., Rubtsov L.; 11,
Sov/79-29-7-150/83
TITLE: Synthesi3 of 3--OY-Z-3-alkyll(a !'I-quinuclidines and Their Esters
Ty
(Sintez 3-doi-3,-alkil--`~ r-11)-khinulklidinoy J ikh efirov)
a
PERICDICAL: Zhurnal obshchey khimi-I, '1959, Vol 29, ur 7, pp 2337-2343 (USSa)
ABSTRACT: Rubtsov and coworkers damonst Irated in ea,-lier reports (aefs 1,2)
that some 2-mono- and 2,3-disubsuituted quirau~:Iidines are of
ng the less
high biological activity. With the o"-,jec+, of examird
investigated 3-substituted qu-i-nuclidines, the authors carried
out the synthesis of a .number.of 3-ov-3-alkyl(aryl)
quinuclidines and their esters. For the synthesis the authora
used qui.nuclidone-3;7thich gave compo .unds (I) by reaction with
organo-magnesium compounds.'In sorriel instanoes the tertiary
alcoh ols were obtained in e,,onsiderably:hig
17er yield3 by the
use :of orgar'Lo-lithium compounds. Thus, the reaction of
quinuclidone-3 with'methyl-Liagnes--um iodide yielded 2776
3-0--Y-3-methylquinuclidine, while the y-Jeld vas 81,4 when methyl-
lithium was used (Scheme 1). The c3nversion of the compounds(l)
into:the esters (II) wan-l effected. by heating the corresponding
tertiary2alcohols Trith acid 4~hlorides. The test results rere
Card 1/2 attained.rhe'n chlor'oform solutions were used for~tha reaction.

Synthesis of 3'-Oxy-3-alkyl(aryl)-quinuelidinaB SOV/79-29-7-50/8.--
and Their Esters
On heating (Id)lcr~some time oilv'h acid :chlorides Yri thout a
solvent the compound (IIIa) was obtaired instead of:the
1
. ester.s.,The ready transformation of (Id) to(Illa)
correspon ding
induced the authors to study the effePt of other desiccating
reagents on the quinuclid4nes (I),. For this purpose thiony!
chloride and sulfitric acid were used. It wae found that (Id) on
short treatment with thiouyl chloride (15 mol) gave a mixture
II1a) -Tith -phetlyl
of ( ~3 -3-chloroquinuclidive which was difficult
to separate. Heating this mixture with alcoholie alkali hydroxide
yielded (IIIa) only. On heating (Id) with.70% sulfuric acid (Id)
gave (III 'a) in 90% yield. Thesubstance (Ial remained unaffected
by heating with 7T/o sulfuric acid, but became completely
resinous with 80% acid. On heatin-- (1a) for a short time with
thionyl chloride .(equimolar propaTtions, in benzene (IIIb) ra's
.Lormed (scheme 2). The esters of the '4-oxy--3-alk l(aryl)
Y
qtinuolidines have slight pharmacological -activity.
There are 6 references, 2 of which Soviet.
ASSOCIATIOIT: Vsesoy-.zznyynauchn,---i-ssledovatellskiy 1zhimiko-farma tsevticheskiy
Lnstitut imeni S. Orlzbe-,Y-Likidze (All-Union Scilentif ic Chamico-phar-
maceutical Research Institute imeni S. Ordzhonikidze)
SUBMITTED: May 15., 11958
C ard 212
A

SOV/122-58-5-25/26
AQTHOR: Podurayev,.V..N., Candidate of Technical Sciences, Dotaint
TITLE: Inter-Vuz Conference on Technology
(Mezhvuzovskaya tekhaologicheskaya' konferentsiya)
PERIODICAL: Vestnik Mashinostroyeniya, 1958, Br-5,
p 84(USSR)
ABSTRACT: An inter-vuz conference took place in,January, 1958
at the WTU (JJoscovi Technical University) imeni Bauman., devoted
to manufacturing problems in the engineering and instrument
industries. 22 universities and representatiVes of research
institutes in the main engineering and instrument 'branches took
part. Over 50 papers were'read. 'The~following papers were
devoted to the state:of knowledge of thetheoretical foundations
of production engineering..."The Basic Trends ofDevelopment
in Engineering Manufacture" by Satel,Ye.A. "The Fundamental
Theoretical Problems -in the Development of Casting",
-U.4i..."Current Problems of Metallurgy and Heat Treatment of
Metals" by Sidorin, I.I., :.Professor, "Accuracy and Inter-
changeability in Engineering" by Prof. B.S. Balakshin and
"Present State of;the,ixheory of Plastic Deformation in Press-
forming Manufacture"Iby Ye.A. Popov, Doctor of Technical
Sciences. In these papers,'the main attention was devoted to
Gard 1/3

Inter-Vuz Conference on Technology SOV/122-58-5-25/26
manufacturing methods which could be performed by small, light,
universal and economic.plants. new production methods capable
of improving the life.of machine components are needed. The
trends of increasing power of machine'tools, greater expansion
of high-speed manufacturing processes 'and the need to ensure
the greatest precision'in manufacturemere emphasized. The
theory of interchangeability of machine components requires
further development primarily in its application to pneumatic,
hydraulic and electrical-elements. ~In several papers, the
inadequate use made in the theory of,iranufacturingmethods of
modern achievements in science was deprecated. Further devel-
opments in the several branches of enSineering .science needed in
connection with topical manufacturing problems were indicated.
Widespread automation and~overall mechanisation of manufacture
were discussed in the following -oapers:. "Trends of-Development
in Automatic VIelding" by Nikolayev, G.A., Professor, corresponding
Member of.the Academy of Architecture 'and Building.~.
"The Automation of Manufacturing Processes in Engineering" by
Prof. G.A.~Shaumyan The Tart Played:by 'Eleetronlas~ ~in the
Solution of Automation Problems'! by Kugushev, A.M.,Professor,
"The Configuration and Classification of Automatic Production
Card2/3

SOV/122-58-5-25/26
'.Inter-Vuz Conference on Technology
blachines and Their Basic Elements" by Prof. S.I.,Artobolevskiy,
"The Basic Trends of Development in the Theory of Automatic
Regulating and Control" by Solodvnikov, A.V. Professor, "The
Application'of Electronic Devices tothe Programme Control of
Metal Cutting Machine Tools" by B.V.;Anisimov. In the present
state of its development, automation must ensure not only an
increased productivity of labour but also a high accuracy in
the performance~of.1ts individual'operation and the constancy
of its properties in time. Problems1of the evaluation of the
economic~effectiveness of introducing any form of automation
under given manufacturing conditions must be furtherelucidated~-
The flexibility of automated:production should be given
attention. The.problems set by these developments must be
solved to an increasing degree.by the methods of automatic
electronic regulating and control and by.programme'control
systems. 1.
Card 3/3 1. Industrial Production--LJSSR 2. Engineering--USSR 3. Instruments
--Production

(Diazabicyclononane)

50)
AUTHORS, Yakhontov, L. N Rubtsov, It. V SOV/,79-29
-7-51/83
TITLE:
0 c
Amin a ids of the Quinuolidine Series
(Aminokisloty ryada khinuklidina)
PERIODI ICAL: Zhurnal obshoh.ey khimiif 1959, Tol 29,~Nr 7t Pp 2343-2343 (USSR)
ABSTRACT: No data on the synthesis and-biologIcal activ.ity of the above-
mentioned acids is given in~public ations.'The following amino
in this investigation: o(,-Aminomethyl-
acids were synthesized
.
iidyl-2)-
(quinuclidyl-2)-propionic acid (III), ~_(quinuc
E
.
aminopropionic acid (VII) , and ~ 3-amino qui nucl i dine -2- carboV.1i_-
fl
acid (XII). (I) was used as an initial compound for the
preparation of (III)(Ref 2)(Scheme 1). The Knoevenagel conden-
sat.ion,of the aldehyde .(I) gave (II):in quantitative yield. The
hydrogenation of the double bond and the cyano group in (TI)
was effected with.the.Pt catalyst~according to Adams and -.-7as a

J.
one-step reaction. The obtained esters 010 acid (III) was
saponified without previous isolation. (IV) was used f or the
preparation of (VII)(Scheme~2). The-Claisen condensation of(IV)
ve
with ethyl acetate
Ref 3) gave the.sodAum derivati
.
lenol foLrM(V)) . ( dissolved in Trater only within 24 hours,
V~
Card 1/2 yielding the sodium sallt of P-k-ainuclidyl-.2)_ ~-ketopropionic

Aminoacids of the Quinuclidine Series SOV/79-29-7-51/83
acid after h .ydrolysis. The oxime ('1I) of this keto acid was
prepared by the reaction of ~the sudium salt of the acid with an
equimolar amount.of hydroxylamine hydrochloride in absolute
alcohol. (VI),-:~-1-3 converted to (VII) by the Adams reduction.
The synthesis of,,(XII) was carried-out as shown in scheme 3.
Against all~expectations only.one diastereo-isomer of,each of
the three aminoacids synthesized was obtained, instead~of the
three thcoretically~possible ilsomeis..There are.4 references,
2 of which are Soviet.
ASSOCIATIOU: Vsasoyuznyy nauchno-i-i3sledovatellskiy khimiko-'Larmatsevtiches-
kiy institut imeni S. Ordzhonikidze (All-Union Scientific
Chemico-pharmaceutical Research Institute imeni ~S.. Ordzhonikidze)
SUBMITTED: May 15, 1958
Card 2/2

RUBTSOV, M.V.; YAKHONTOV, L.N.; MIKHLINA, Ye.Ye.
Hofmann degradation of 1,4-bispentamethylene piperazinium
dichloride by means of a methanol solution of caustic potash.
Zhur. ob. khim. 35 no.4:621 AP 165.
(MIPM A: 5)
1. Vsesoyuznyy naxichno-issledovate,llskiy khimiko-farmatsevti-
cheskiy institut imeni S. Ordzhonikidze.

a I$ * 0 0
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it of 0.

!nd J :Xkim. Farm. Prom. 1935, No. 1.
"
k .00
prort neetbud in which aniline Is treated
E
R .00
a
Sk
pp. the quhwline sullated at 100' with
o~
00
aleum, treated with C&C% and the Ca sale (A 8- -
ImmilliwAmllue is decouipamed under with N%OH at
2251
18 -00
-
atne.). The ppt. 6 If in dil. ",SO..
exiled
Wtcrvd and h
drox
uin
li
d
i
h NH
.00
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o
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t
y
nc ppt
, and
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A
LITERATURE CLASSIFICATION ties 0
A S 4 1 L A 0
TAL LU
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L

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u a IN Cr
It It 0 0 I
1 K It It 9 PC a a it of an A
el, a 'al W 0
0 49 aff Aw ma WjK W

IS a as ISISIN a noose or - - - - - -
P.A lop 4., C.94.%
c.' eery& m MY,!tuvmv
lee
(J. GsmL Chin.--gumm. 1937, 7, mg&z;NW~-
ON&oCW= )4XS mid p4nisidime In &q. AcOR yW
IMFItrump (1), M.P. 120-121'
whil&L in sq.
j (N4* Ad
I, 7mar ;_ Em
KtOlf-AcOlf 16 0, P-41OW440-Oft'-di-
acr*k (H . *.P. I kfir Amrivauve, M.P. Im",
(Zoo owkd (1) f. Vo
so
go W(%- M.P. 57-47-S'. of
=;9o0
(1) is by bewwa a 10 as "Ution of (1) for
20 the resulting solution to fight 'o6
heated at IW Yields MCC"-
me. ago
is I
go M.P. 99-101l" (I).
goo and U~ TlW N-Afe dwivative, M.P. 37-6--W. nr
P-0 SmIlmo, but ught th" 011pewtAwl
qu what healal with H(X,'4. (11) lee
w 10% in ~IWH affonla 1 ."wimV14-
plic acid, M.P. 25r (chkriple
P. 225-11 m4'
U24-146% #Now m. W ; didA;i;.. 0
118-5-41*50. RIF 684w, M.P. 99-401-15") from
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wridlaw, M.P. 110-111 is ob.
Wood by alone at frome Zn dioL be*
:t R. T. we
ago
L A
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19 934MI WWAAW
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0 A
0 t
:
lao" e compounds as sources of medwisaf -00
Vl?"Andmalarfal compounds with tbo side =1.02 77.5-8.5.:
four-Poslition. o. Yo. MASIdsurt slid PicJif and. -y-dirtkyl.
0 J. Grs. CAWg. I It I -hydrolypWpYtarnine M form 6.
;. S. R.) 1, nitairzy-4.
A'1 C, A, 31, 811.31-When fi-melintyquinoline N-a (-f-didk*N6xv-O-kydror Admirindine which 4 0
8jImithil with ~A NCIt it furritti a inixt. of quinoline dich side Is milly absorbs CO, ...I YOr from e air. it I 1=4" -00
krisirs, tts. 210 -1.1* and its acdAted p rate in. !Mw -7*. U 400
till. .07, -8*, 1 IA.S 41" anti 123 4' (Picrate, in. IM-911 give the comsitonding !4romef th 214-0', m. 9
If POCIs is used instead of
S Pitrate m. 1110.3 2': di-110 salt to. =00
hCI, Ottly 4-Chloro-6-joetholyqUin(Aine (1). tn. ".9 0.5", cumpds. am fortned with greater difficulty and in suaLlet .06,
:o c, anti 2-chtoro-d-metiminyquinoline (U), to. 1064", are yields than their Isonterp in which the 44k chain Is in the 9- a**
iGwored. Ilse total yield Is 90% anti the ratio of 4- to 2-
1ri,nip-1. i, 7 ; It. When I is bested with I -diethylaminot
4 smint,pentane QU) it gives 40% of 6-ndiwxy-4' position. The 2-isomt-ri harv no antirnalarial action. Ce a
in. 12T The 4-imaxners an, antintalarials. and are less toxic than
40 :1 %V; j~saau. m. 11 and M form the corre- the 8-imaters. Introduction of Off in the side chain fit age
The 4-compds. lowrmshe toxicityand rvises the th,-ralicutic 2 go
00 17),.-nding 2-immirr. 1), IMP -72'; di-MCI soft. tn, Vd-101 index, which is exactly the apposite effrct from that pm.
VFW
0 alai capillAry); *rate. m. IM-4*. - With &Aiethyt- duccd in the H-coonght, bv This chAnge. If. M. L. zoo
00 L' i4minobutylarnine (IV). I fornis - 31% of 6-awk-
Th M-7" M.
It and IV give the analogous
:so 0
2-imow. bt IMU'; A-11CI jaft, ru. I97-9'; piagir, m.
A secondary product of this reaction is 0
M. -_199
.tr L U G A ERAItRE CLAIJIFKATION 9 z t
7
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:

- apill I PUT TMID ql!A 'PIT2 PUT saluisirsiq ojut pjlj2A

3.0
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-
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f
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d
f

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ll 1
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o )a
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stiuj e 2AV 911-6 bp
-
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A
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- 0 0 0

r A 314A J21W.1 1
4 uadtola"poutoill.1mu-1 Pug a)vj4%fxjjv.)
=
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pjup"Ij GVA U001.7c "12111sau
'ilia Pal-"aJul it""'s
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l
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pd
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q
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r.
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R 91
be
.rtis w
at swas ,,, -1 inj pat.41rur is
jo -4ma
'
'.1saktill
1T
IA
t
I , 10 J3jSUUJ] 241 10 13J114 *101%.(flif `
,q.L-
(
(11
!
%Saanal ajjI.WIqN C 1, nup.;
,
. N
"" 'AU!U!nb
,,
9MI-Ntl '6 ('11 'q 1, -no,) 'AOW (inn
'
Y
I
-!q In -113 'bv ;Itl I WtTl %w-vi
7
. -PISAA001 polo
luml 'A 'to -qi a m f jito uln b- R-.Goqta ~i - 9 1 (1 xplp"
upilt as
so- ur
f
-,1jpAq 10 janum -r-14IN-51 .1 sulaliaboi pAq 10 gjamoul )a glutalpa-4; I a

roe
0" 1-1111"al
f Tj 0
IV pt II to of a of a $I a v fq Is It alg N it vow It -it ps, 111 "1 11" oil .11
4.111111 0 0 00 0 0 111 0 00 41 9 0 .4 111 i:#
! Iiii -4 if a
- - - - - - - - - - - - - -
111 M, I It 9 1 1
f
ir go
I II Pills

III W IF a 0 9 W 9 a W W 9 a a III W a w a . . . .
Col-01 904 64
f 1 6 1 0 1 IQ it 11 is Is it 4 it R is v a 201 21P un Jim by is
:
A A L -A-L-f
A - 0, .
I-" CC U I , . I ,
-L-L- 1 -9 -u- -L - k
!-D -of s
'.

O-Arylausinctacrylic asters. U. Synthesis of V-&ryl-
4-pyricloutt-3-earboxylle sefda. bL.3, Rubtsov. J. Gem.
-
CArFFF.(U.S.S.R.)9 ~,,
.39,620, '
;fi
~

0 -By followins pre
s
racedures. 0-arytamintutrylle
ester Pfri -bjr Coll F 't
2 am
Untsation of HOCIVOIC(itl"

t
with 714111 In dil. AcOll-, the r-Acts on licating in
-0
0
V.14 k, to- WOW the in. Pl. ructit
COVIS
these when sapond
with sk
KOH
lize to .
$00
.
.
.
l-4-p
Al spocidin N-ar
MMOINE43-rubox
l rwiif,
z

j .
y
y
I
tfir )rep". of X(Y-Fiaphil
~ -4-pyridoxf-.11 orbo I Wt. =00
00 j~ v
I And 'v-t4rFIy(-4-Pyr (111V 46*
!
j. I itil 11114rdiAle I INA11.1 not 1W iI-.1-X'IPA$4vV

'
as*
01CF, ICA11011. III. 134-A
. 11 r%t,to tit
wmairric finieks, its. :kit;-7* and 2152-3'. which were I zoo

0 -4
00 as the X salts. ;!-Axilistoacrylic ejkr, in.
'
;
nredles, tit. 20-4
. P-6-Quixolyfaminoacrylie ester (froff

001 6-aminotitsinoline), prisms, in. 155-W. The diacryie '2 0 a

00 2 rjur, needles. m. 127-8'. yvidont,7-
i
id
3W-V (
b
l
i
kh
ik
l 0
far
, ac
ni.
t
, powi
w
cr.
ccumpri
; c
.
are
D ester, III. If;-17*: dirtkAisssiJt, tit. MW.
, r

4141 Most of these compile. are pale yellow of different Aside%
i
60
1 . , . L .
1400
00 t:0%

S L A AITALLURGICAL LITfI1AT%,W1 CLASSIFICATIC.
00 0
%Iil;.j j- ;.t v I I A
alit
u O

a 0 0 0
000,000,0 PF IV et IF va Kit 0(99 r(fin 1901
0 0 0 a 0 0 0 a 0 0 C 0 0
000000000000ooo "LO
1 440;
4 0 0 0 0 0 0 0 0 0 f 0 0 0 4 4 0 0
so~oofooooooo$O*Ooooo:~-

is Is X it
it A X is it U IS U a III V 31131`411 43 4143 0
4.80
A
410 A I L
-L-A-L-A-L-a 1i &-a
a

00 - 0116C04111 AW Vile,01111"is ..oil
c
U us
IWUVT~~y CsowJcy, ri d. t C. .1, 31. Kkill). is
Chemotherapeutic Th
Pr*Pxrstloas of the
"savOicids"
l
e gcnrf%
pt re
riescribing the following cuinpds. di
'
@tries. 1. Azo compounds.
0. Vu. Magid- -4 X
i
l
i
f
I

0 um 10
Atim
a
a
on o
.- ennxists of a C04p
ins Itut
lp
V RUbmw
C". (U S
8
R
) 10
769W

0 -
.
.
.
U, culn ter
Ij,,NCJIS0,NIIg (VIU) with a rt ired . t
(1114OL-T r study of prontusil, named hem "strepto- D' ' k
&1 ap= wik:
d
) bensexclX-
4
-00

0 2 en v
w
Z
cide" (1), and its derivii. began by prepg. 30 aso oomptis. SOIN . , ( , .. 2:"-
j N11C.11 if j
g
of
l
d

. aria
ogous structure an
j
computing their physial. e&ct ii, (cheincitherapeutic index 55). derived Inxn sul-
on Mice infected With hemolytic stmpt in the fandylsuiranilatide. M. 125-7% prcpd. by refluxinc,d
parallel tests the chemothers
ocutic ind
f I
t
k -00

0o a ex o
was
a
p
en " hits. 11.65 C. p~AcNJICJf.S0%CI and 172 t. VM In -VerC0
a unit - 100
Th
l
id
h
-00
.
e cipt
. ev
ence s
ows the Infineam Of
and sapong. the coodcasation product with boiling 17%
the S0lNHj group
since its replacement b
'
0
UeO and
i~
0
041 9 s ,
y
,
-SulNm.W.2,4.diamixwsobensMe(M-UMploci
HCI. ?
.
LtO groups produced inactive complis. Accumulation saft, tn. 219% prepd. from M and diazo-
-
f b .
0
oo
2
09 o
ewentsulfunamide- groups as in U resulted in decreased tized m
4ulfanilamide (cf. Zinckr and 5filfler. C. A. 7. g
activity. Similar results were produced by transposition 1720)- Index W
of the sulfonamide group from the 4- tz;3-positlon
lathe

) .
i st
f th
d
i
i
l
W
f zoo
00% u
o
o
.
uencr o
e p
lys
the 2ml &to component M-W. prepd. with
; ("gU(Nif0s Uff)) in I the substitution of I and 2

u L7tlNCIjlCjf2NjIPh, is toxic; index 90. 4 -Sulfamyt-4-
OR for Nil, resulted in inctrAwd activity and toxicity. (jjiejAjdamix0-z-kydrvX protyrami"Odsobense", M.
W The replacement o(IU b
6-h
*
drox
uinoti
d
a =00
roe
:: ne gave a pro
y
y
yq
- IM-7
i (ujI)ClItNHPh), I% toxic;
(from EtoNCl
(
Uct 0
high activity and decreased soly., and that by 6- index 100. 5-p-SullaM.Wphegyi4=-fi-kyd?OXYqUiROii
,
aminoquinoline gave a product of an e
ual a
tivit
d
M
;
c
-
y an
q
does not m. 2D0% index 100. Z-W-
-SjdPYIPk,-
1 2
greater soly
as cam
ared with 1
The
f dk
h
l see
.
.
on o
p
t
- Namixo-l-xapkIA4-J.6-ditulfanit acid prepd. with
,
y
sminoalkylanilitic as the 2nd component gave complis
with
V
I
.
I
). index
11 acid, is toxic; Index 100; tile AC deriv.
(
higher toxicity and considerable chemotherapeutic action 100.
against hentolytic Itreptococci
'
tr
panoso
es
d
"I C*

goo
, an
m
MA
,
y
-SlJfaWlY-
kiedrijulfook acid. b ck powder; index 40. 4
l
di
C
asmo
um.
ompds. formed with C1.11WS0,H)s and 2-amoixio-4-hydroxyasobenseffe, M. 228% index W. 4'-
p
its Mix and Off dcrivs
-
showed var'uus de
" of
h 309
.
c
emo
g
Sulfam acid
therapeutic activity and, with the exception Of IV are
t
300
i
k
W1
N
CO
lf
d
t
ox
oes not in.
(from
;
)AIL
).
%
l
4
. Tile 0101t active Preptis. Proved to be V
f
rom re-
. Index 85. (
V1 and V71. The name systein for sliffandamide
does not m. M)0% is toxic: index 100. Y-W-
sorcinol)
.
1 ISO*
-
LITERAILRE CLAS foxic (from chtomotropic acid) index go. j (4
-- _- -Z,:
5 0 - S L A mETALLURGICAL
I
till 0
,
-. -
via-
woo

SOJONJ 1.40 0.1 04C
4"
r 4 . I
q
tr it 61 K If 99 K Is Its it
1)A F An L 1 9 1W a H a it a 3 -V-v
11 1X4 d"ej

4 0 0
- Q
1 0 0 0 go 0
0 0 0 0 0
0
0 0 0 0 0 00 0 0-00-4

- - to 11i, 6 9 9 9

I -
was purificd by beating it 15% IICI.
'
t 00
acid). m. 220
(decompn.); index 100. .(41-Sid agayi.
-n, soln, with dil. %1A,COj and7etTysix, Inion
dr1i4 (frrom an nille I
tn 00
,
. Nle,CO*. Indell 71), 1 At-5,41ra" VIP*#" Vi'loviva) '? 4ilk of
11"JIV-4% lnfl~% role It, M. V. Rublosiv. lba. X11-43. d-oio
b.w,
it '
0-2 1
n
*0
,
.
-E*rivv, a4 VIII *fill w4lotilurnis In tho orultoo 4nd out- 1 11 1", Iw4tills t JAI' 1-o A Itt.- 1. t..%I,.
itr
I tni 00
latuyl sloulill VVtIq: picthl. *lid their hysiul. tetkno were IUkz 45, 1 -(P-SX1f4 wylp4flo via M i~) -2-hydroxf,444A -
cumirAted. In the ;Wfillk-I trst.-I t9c chemotherapeutic ICHCII(OIDCIf
NE
ICO
00
, in.
t,.
j.
index of VW was tab .n as a .unit--SO. InIpricral. t IhIc112'. 1; to;dc: &Idex 10. P-Sutta-~Ip4evoyftlyci. (IX).
26"'
d
b
ecompti.). was prepd.
y gently heziting 7 g.
(
therapeutic effect varied with tht nature of the substituent in.
a in the amino group. Introduction of diethytimintIalkyls CIf,CJCOjH in 15 mi. of 2U70 NaOll dild. with 2) tn[.
0 decreased greatly the therapeutic action and inimased the IflO. 7.5 C. of cry-st. NaOAc and 8.6 C. VM and recryug.
toxicity. Acid radicals, linked by mr-anis of a methylent from 50% &1c.; index 125. P45f;qp4ex clwis'l-laf,
, 9
fl
d
o
In. 11
1
. by re
uxing and ILCICONII,
00 group. mcreased the activity and qDly. as in IX. The 203-4 was prep
in CJ1
N 1o; 2
5 hrs
with 2 vols
H
dilff
0 and acidif
in
i
X
s
.
.
..
.
*
.
g
bewyl group showed but little effect on the activ
y
).
ty (
00 Of the muhstituents in the indfamyl group beruyl produced with HC1 to Congo red; index 83. Na .6 ml aft(phesyt -
W
i
"
l
I
8
= 00
. land
famaze wall prepi
. by
ntroducing 9 C.
.
j
00 an insignificaut change (E). while sullaggilyl and s
NCOL g. YM into 50 g. C.H..1; at 30-W'
treating the mixt. with
-M
Vlf
d the activit
Tha
t1
d
Cjf
90 at
,
uce
o.
grea
y re
y.
a
~,
p
of group increased the activity (XU and IM), which again 7.3 g. NaOH in 15 ml. H10. crapg. in vicuo to dryne4s, to

'
00 was reduced by the presence of SOX in the auliq6tuent dissolving in 40 mi. 11,0 and cryst at 32'; Index 3).
V1
11
C1r
V
N
1
O
l 00
a was
1
u
ruted by tre-Ating
a
oS
o
s
XIV and XV). P-Salfam P-
OQC%1
mine W, m.
=Vb"14
of (
17
2
7
with 9
6
f
nd M
of 50% NaRSO 00

-
.
.
S. o
g.
j
1
1 6
174,&-76% was prepd. front X. &H, 6 g. VM.HCOff
- CtIta
at 12o-5* 38.24o H in 38 lid. 1120 ans stirring the MiXt. AE .5 1'
h"ting the mixt
of Ah% HC(hll b
as and 7
5
of
.
.
g.
y
in an oil tnth for 3 his. and dilg. with .30 mi. ale. The for 3 hrs.; index OU. p~NHlCgt1#SOIXIICII,Ph (XII,
1
of
in. 11".5% was prepd. in 94
70 yield by s4pun. of p-Ac.V-
04 IlCjf.SOtNI[ClilPh obtained by trelgiing I I.-, g. P-00, too
SCJfNJIAc and 10.7 g. Phcjl,Nil, and recryllir. from 00
00
W% &k.; index 05. Dituffandimide. in. 293--gl' (de-
00 compd.), was prcpd. by a modified methtmi of Crossley.
d d. (loc. cit.); index S. 2-Animo,;-j;dfizFid4m"A"-
00
index 110-
Cro~
as "e c c1.) .

H I
,
00 index
.

-
gg
(
B
2
00
00 f". i,.
)6 lid .
-k. IT 2- -81,
p
g~r
25
i
V Ul
.
.
-
00
00
00
00 00

9 ~900 9 fro 0 0 0 -0 0 0, 0 0, 0 0 a 0 0 00000 066094
NNW

I
RUBTS011, M.V.
"Chemo-Therapeut-ic Substances of' the Streptocide
Series-II.11 Zhur. Obshch, Mim. 10 No. 9, 1940.
Synthetic Dept., Scientific-Research Chemico-,
Pharmaceutical List. Imeni Ordzhonikidze., Moscos.
Receivc~d 20, Nov. 1939
Report U-1627, 11 Jan. 52

a 14 0 4 V o u u a a if! Ali
9 do K_ I_ _R _L _A _u It If 11 1 All
11111 fit
-%*4ijjrd high Iq_t)jT__
Syntheinsolisonitrsotbydro-quinins. 11. 15-2161, fit cry! .1. froln I",', IICI i54 or., In. I&S ?,~: 4~1 tivul.
quiliuclidyl)(h-Mrtholty-2-quinolYI)CArbI. IM1211 "Illf 30o'; Natill, Own- %sa. ohiaiiml It. t;. All
so A imtv, J. Groo. ( hem, it', S. -1. R.1 IJ. MCI IVIAM1131 hretk,,.%,VY01.'I'ditiow. to. fill) 711'. fit, 5x' (#tude), o1, #117
9 jVngli-ls niumatyi; vC C .1. 34, 41-Mviltoly- P iftialt locar. Wthtf): 21 a. 0I the alklIM, 1111) X. 11*11
15 o(. CUCN 410d &I K- flyfidn"' and A X. Z1 cl, wvir IT114111.11 f,* IN tn'.. 111.1 "till
0 ."t, 1. IUmA Im f; 1.1" i III$- ~,lld Ilia" oom. nliu-11 will, %lc~ctj and treated %till% lilt. the Ilytyi $%;?at,
If Ill ce'l I W , I I C1, I hr pitt. fillcred off, %railicil with water which Win. was fiftered 41ty. WeAtelf u ith N(C.0 gulct I.A,0
fill jjl%~Ivcd is fill hear tit AVOI I : tile MAII. to as -allf. with still flaitted with excess 151*~ NSOII. tit Virld K-Welhot, ".r- -0
00 a-5 to$; Alture'l, '4114 tile filtrate dild. %Willi :1 vok. 11,0 lo, I)lYpilpf"foxe, tit. 1.50-l" tfrom Ail. livrWilic). nor 0,
jr r*l.l 7.1 of. (1), off. M, W N-ve (I X.), 44) tv. list h still 11 1 N sit. vftclol~
lit. tile
00 Iffooll P10M. 1-1col"A Willi V.4",& IICI it y1k, 4141%. vtrtr heated kill A orom twits 16.1 1.1 took , 4111.1 unit
00 'at" and jjjto~le,t w Y104 I"Ith it Of.. I.I..Ikht
tivat"t %kill NaCN fit flonj tile inother ltqxhots~ uns it.
011111 %IrOil At [,-'1 '214"', gavv m, M.-S- -z~te. t-ittstutitatot -i th 14011; the latter wit, r%td,
Ile*
e -3 ff,,- Vitsiff. 1 (1.14 9.) isn't 4.1 CV. fwl"~ UrR)a with Viol) and life rttfiflor 416,U)NI'd ill X NA011. filt-^l
heated ill go-11111. 1.111ing for :1 lit%.. dild. And foldde alk. u.1 at's-lifi-I ivilh IICI, 1-1 virld LN it. 111117. In. 2117", roe
ith N.Ml, fill,1-1 '1114 arldifird vifill MAIII, lmvr 11-Mrill.."Y'llfillolitir I Ill 9.1 um. 44drd I,# fiAl a. KCN oil
6-melk"TV Coo
alki (1.J110) 111), ln- I-S-4 8' Ut-alk 4(ho re. "Atrr And tile 4.11116I.i.ill Ireateil "itil imp N. fircl
-water); '119,1 mit. In. 6_1170 (414VIM11110: EI or.11tr IM), added over 0.5 hr.; after stirfing.3 hr,%. the iidid nta%s WIL.
frian the acid And Ftt)ll in the Pleft'llce of IIP50j, TD- wft%hal with water. then with fire IICI. and treated itith
ILji *W tfromis Emill. , lit 6-tuttlimy-t-hydroxYquin- cl,o,cd. IICI with mirring; after treatment (overnight. the
9 tot.l.te (t.x a.) ,,.I Im. ev. 11(Wl. werr gently boiled flor tiliq1t. "as filleted title ill's, "a, lit-JI'A with 171";, IICI
J.mr.A .41 fee and 61felftl lit Yield A X. 11 and clicht the 111.11, part 4,
Not, off- lit' Conly after r%lrn%ivc1 IICI, In. *.,tt~;. tt*l anti else mja. %td. wtilt CIICI& 3 tittle*
Ir-mol CIICI.-Iwlr. offer and ioltAIIII); the t"Fre. it) remove flail; file ail. .4n.drimmird cry-tali -it 11.11a. WOO
readily off beating will, which virm augmented by mrint. of life sishl. its hill ec.: too
N0011
J fit,, Fif raer Imirumenatcol in HtUll with a total yfrill _13 X.. Nn thm 421..13 X.) ill boilitis IV,
I'll ratitiv-1 Kim' 1'0'. Irne %ait livalril, after o-mlinot, milli i.11 ji. I-Allf mood 0
t into. I It, It 2. "0 Co.- mIlvd. 110. MW rv~ water &sill :m it bellied 1..t :11.5 Ill..; tile N40H "a- formed *fill linkling
'hLpv well, 11.141-1 it, A It. W Ills. a M It. ill, A, too M_,inj .1111int "ill% 17, it Ill .11.1 1:1 a,
to
atIALLU*GKAL LITIRAT1,01t CLASSIFICATION
IL
zizi 411041011'
S111080 "it 0.. Ong 41111910.1 1111111 CK-4.1 All
--f 1 -1 11- An A S 9 rW 4 9 1 W So a
U tj &1 10 LS to . ag ala 1A
no 1W 0 for a 1% it V or U CS it in
0 a 0 0,11111, 0 0 4111, 0 0 0 0 0 fill 4

T ATIM-)
the me" vqloj~,l .11.1 0-1 fill 2Irlp v.
4 h1tri"l. urlhl (tom Fvlrnr Aml firntly 1--ifeil low 4 lim,
so
so VOL Willi FIFO milli IN, kill, -hl. 11111,1V Alls. milli Ill,;.
i
l
d

. W
l
l
.1111401.111pse t1[
NUOII, tile 1"llting I.Avdt'.
06 FtA) skn.l Iluritit'l thmugh Ifir do-1114P tall (its.
*
-.
trvTpirl. frt-tit F'911)11. In. 195 *,'; dipi,rale, its. 1117-8
111.1t.,11-5 M"~
06 M.'"o-fin 1,111
.
*
so (5A7 S.) fil I0 vv- III, - 11111 %a* I .tralrd at 03,711* Willi
'
of
iSk"t Illif MIld, %Vita A-14IC41 61FI111-
ill
10.1 ji. of 0.13"; llr
00 wiw over 20 Itlin.; tile llbi%t. wwq heatt'i to NV alul
06 4tiry"I at thin trim). f" *-41 n1in., and the c3crSA Ilur re-
00
nusy"I'm men. at 'A)'; thr r-idue treast"I %ith 10~,~
00 NmOll unit exist, with 1,cutrisr, yield"I oil CVL&Pnl. Of the 00
04 I-SIfrI on.[ lrvly~lll. (Imn
00
so
"ft'~Jkly th" "Ollit'll. (iNAPY41,1quix4rairel
r
40
in 1hi
; Ftt)Ij ha~ n1ji,
stand-

f
00 ma -labillIC4 at 1"lls
- 111C UIN)VC jd~jt; 00
IICI wit' IF-1-1 -012"v, U" aflvf~!;Alkinfi.
so
i1
;
00
11111
its, vrlllltq 1,1,1. na, 1h4n4lj
gIlIv .1161-cftil. 8 m
00 11,.0 ated 0.25 C~ activattil I haroull werv allilett And tile 00
nim. hydr-pmettattil at ri%lill 14-nip. unilcr stailif If prc.~Urv
04, mt Com
letion
l
(
h 00
..
, rritu'va
t
p
evatalym and allitin. of alkali
1111110 Ihv Im.111vt wit, ~%tif. l. Ith 1;1:11. Which 'its rValln, Yielded 00
ItLa-v 1111%im'. ..1 1-11will (probabiv
00

d A~. 00
06 c1l, . cit c1 I I:I

cill
NIVO.,
f
C I I it I I Ic I I
N
00
(Al

0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
0 9 9 0 0 0 0 Ill 0 a 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

0
-;-0 e Is 0 A U
d 4 1 1 f to if 11 is IS is Is of Is NO a I u a so a is a a as 11 it IN 3d 1111 m IN, a
'i
As " ~ml I I I! AN 111111 Cl Iff ~!I' !N ~Ar .1 ~~-l
A I X-LA mpg_,& I I I , A -J
1 3-
4 1
eel "hich hall I-- I V III A' it' 04"; R'1011 - JIY ItIvAl"N -1 di" 61ur hratc.1 la)vj. f
tribsil loss IwI% eel' 10 1 dod Cl lCh 411 'lie Iteld 14"tral" of 'and the elk .4 IN' I h"N- Wall r1ttl -00
( .. IN. *a. it",
tIll* i-Illerie Itlikit., 3 llarlh)115 were obtained, stv follows: Kill'. of 11 Sup " h wait.
09 ,N .. Wall the Wll craft, I , * "sib r
frool all. ohl. there wa~ ohtaill~t a Khm,"y mass Yield 1"-11 Oranife-colored 0 - "it takeso "It the,-Ad,d -00
uP with -00
ill Vies). 1.11,! :0,5, (inimlol~ M101.1 Piii rate, it (B Et'O IN; z N"i "s
tit. I78.5-7t;l i1r,gil !he base lifirrat"I train the
C11,01.011"t
pi,lalv Wa.acurAmel-Kv ota., Wish
V; ill*. nimlivi 141%un% ficitst the picrate litell". CII,
00 IVAVVA thfIRIKII thri-T4141te. J
tit. tit-' 1'. anti yieldr,1 a Kla-y masi with J,.JJ1 -1.7. 11 elf,-
(IIN6 flaw "N~ flai the ev"opii. (b) the
z elicit rill. give a gla-y ImAllet, which was Purified .1
I S- ell,
-_~C,
(III.Alith lilt- prate, !It. 190 '21% atul Ox4late. tit. 1711-61.
-Ttrif tit A Itirly etyst. %OIW. its.
anti vtolvi I
go 0 1:19 1'. Tlsts~;l wpuratc %terciii,imucts it( isohydroquinine
Arre imiiate,l. 'rhe steretoi-turr suist. gently reiluxect
of Wish ;5411', A.-Oll. Olilfl. 41til treated with alkali, followed
0 0 1 vmwrr~im just, If lit all, Jtavv the pre- If age
by all,
vi..41,lv 41-cril-I al. IINAVIl", rise
9a Which WNL% hydrillylett with l"Alitlig 17e, l[Cl fia- I lim, And
ill. i 5,Ethyl .1 quinuelidyl) -4 -pyridylearbismal. Ibid. ater leellovitl of 11SOll thru'lls. ltva. talk. and C%141.
NiVid (lit -
"tth lit.0 to yiehl, Ink leol.,val of litts, X:"
X.).30 ce. At". FtOll milli 1.5 R. c"ned. 110J. were heated
-title tvilux, rmleil, puired on ice. trtale,st 4-PiP-&dYl),AY( 4-.6yrodyl kriolir, as a Yellow A; Ola4ilr.
for It, Inin. I., cc COO
with 241'; N11011 t'. %eak Collsit) reaction, then with Kl- (front arid oxalate, No. val.
Tle abov, ketone 13.711 It.) in 25 cc. 48~,j, If Dr was trvat"I We*
C(h t,) w.-akly ilk, rrartitm, extd. with RtP anti the a
t-0. di~vl. in vichl FJ inrisirelimair, Is. 21*-19* with24K.-I! 11).W_; l1rin-1811 Hilt; aftcrisrut.
Htova (from :!.I g. sit its at- Pilo ww. treated with I at SON for 15 tilill.. the usivent was distd. off ix PUCIal
1. ivotinate And 17 st. betiloytholnoduchoillipuric 0
't i,oll
1
t S Ft ter; after stirtinit for 0.25 lit.. the 1-.t0 was distd. off
is
A S 6 - I L A *ITALLURGKAL LITERATURC CLASIVICATI"
114"m Ire 0
.190
1810110 WIN Cv ClIt illtkalls-t 1111111 GK 0" ANN
t I - I I I I a pv -1 L ukal 00
AV M3 451; 1 1 -
u I tv it 111, K 89 19 ill it PC KIN, It A- 11 1 TA An L I a a a AN 0 1 YJ IM 2 a Ir fit
so 0
4) 0 IS 0 a if 0 0 0 0 a 0 Al 0
a 0 a so a 0 a

W6960686*0090
0 0 0 0 0 0 9 0 0 0

and the residue mixed with 10% NaiiM and EW; evapn.
of litO pvc 2.9 g. crude prodwt. Puri&A by warat
S
k
l
2
d
W
-
-O
W
A
peti. ether to give 2.2 g. pure
y
UrWyi kitim, in. 91-2'; the fresh soln. =1164 MIA
60
bi
a
;
dl
Th
O7

00 W.
x
t w
ecarrewan
1
trt4ghys.l.)V
,
.
im
prelki. by hydrogenatim In the presence of PdCls and ac-

0
tiyatett charcual in N HCI at court ttmp.; the restitting 00
n!Ixt. of optical iwitters al Ow earbinal was obtained as a
'
. &M. was effected
VL%Cuus man with jai)? 61.4
lf
h d
h
dd
lt
d di
t
i
b
h
ib 00
e-
-camp
urvu
cme a
va
s an
s
r
at
ott
t
roux
tween water and CHCls.:,TIIA- 3 isomers cd the P-rthyi-
00 2-quixodidyi).4-prid swAssa thus obtained had the

~
00
09 folln
M- 171-2, (from literco), Kv
'
51
b
7
2
2
13
f
E
Oll
4
00 -
tit.
rom
-11C
saU at.
.
t
87.3
1
(
)); (
(
*
'
(6-11CI MU, m. 202-3
WV 34.3
(fruits

L
and (c) in. (from petr. ether), JaIV
'
126.9
(di.HCI Ian, m- 19" (from EtOFI-Ifelco)).
00
00
99

90

go

01

0 a 0 0 0 a 0 o 0 0 0 e a
- 0 0 0 0 000900 see*

U r OF q
I 1W I
:3 1 14 4k0 4f.
04
V
c*;W
Itubtsov and M. V.,LitTn . (11y:k
S. RI-b. 097-7010 go =S~ muststary).-p-Anisi-
dint (24.6 1.) Is ollud at room temp. with 3 0 .6 a. Ht%-
00
M)CHIM13t; the teactiou =1 M ith kc.
cr I . 1=
Matiott of 2 layemil the on 1 "ter,
.1tied in %usa at N) and mptesents it 90 Yield otu.m. .0
ts"J"If. The above (W it.)
to W K. vwwline hestal to 2M*. so
'j . heated for A tnin. at 200% on rolling, there was ob-
00 and
taitied 60% FJ
owed ItY =00
(fronz Moll). Hydrolysis I - INSOH, toll*
M
acidificatitm by IMI, a Mutitsew Ppt I*Wly
Chen i powder of 6-mdhoxy-4-h 00
0OW MUIP-, ell'= 0*0
r,;,. M-4-; . leftine th acid
c0l. to rield in Galva Yield; COOL
brating in me" wfth a antall Bunsen fisme, followed by
cxtn. with hot waterSave an the crt., 90%
tl-tnetbory4 mot (from water), wee
'P.0(
The above (10 .3~40c%-. N, =Uy red=ed
t
for 0.5 hr., after which the milt. was =led with
ke-water, fitteml and the filtrate made watral
with soda, filtered soin and made alk. by w& Tj*I`d it
rkh. ppt.
Ala.ILA MT&LLUNKAL UVERATSWE CUIUPICATWX
usaw S-I"Es'
"NJAV
WON 041F One at "It"s-9
GIALAI lMK am
'A L I
cp a 0 Slit UnIts lean
0
------ Of 0, 0 * 0 0 _ 2 .. . 0 6 0 0 0
40 0 see 0 G'* 00 0-0 0'0 0 -- G 0-0
11 416-18~0 : Gig 0 0

RUBTZOV2 M. V.
aSynthesis of Compounds of the Quinine Type. III.L'3-r-.thyl-quinurlidyl-(2)-fPYridj-l-(4)-2
-Carbinol". Rubtz;v, M. V. (P-702)
SO: Journal of General Chemistry (Zhurnal Obshchei Khimii) 1943, Volume 13, no. 9-10,

Meftyladeout of M. V. itubtowoor. J. Gen.
low. (U. S. a. R.) / 0
(
0 Ill 4 1
I .
-Xiinthine 6 iroactily Purilleal thorough the Na kill try
olor-
ld
l
I
h
l
9
so t
, r e
s Also p
e jolvi
uct
y c
Widilleation by AcOl I, t
101% NaOll was
) in 39
6 j
u
ithine (5
p
i
'00
00 .
.
ure
n
as.
C.
treattA at go, with 13.3 S. AlcosSo" %lifted for 1.5 ht%.. '00
cxtd. with CliCh and the tell" evapd. to yieki 51.8~1' -00
0 a caffeine, in. MI-45% which. feeryst'l. from water, us.
'
'*
*
151,
l
I
n,
n
cc, a
;4-4
. , j P-11 g.)
-
"
240~
KOH
12
i
h =5
k
l
,
a
.
.
wag tiralro
w
t
K.
U1011 of (11)
00-1 Irl solaski avc1night. the K kulli"I.1tv fillvirst toll I A!
with KtOll to"d the dillsolf evalki, 1-1 tu.oia l!) 1.7)
t. "
00
00 4 1 ,~
it third with 15 S. xanthine follovint by rapu heal a tow
1 t [it mixt. was istirmi for I In. at 120 A1141 -1 luss. at
000 1411% wid&~grssdufid 44ta.'al H101 1, with swohlow-W xyltno,
904 i-iihs: thk-k%Rm1mARt.#4-- After troroxintent with Wee. watcr,

411. 'AA4
to
-WHIcatiost by AcOll ¬ mrstin the an
goo
00 .
and the letter orvistool
its
tive
WitbX11CL
l
d coo
09 st 11 .
one
.
I
.. exU
,
11% caffeim. ~ MaRlItylation of the I'lo bell of xonothine
4 by hfc.S(h by rtillizing In stylorno: low[* lot it mixt. .4
g
p.-oviduthesibramine SAW stanthinor sit, clustertusity wall. oo
Similar methylation by %let trails mainly to tbesibromine.
k
lkl
i
x
ne stwth
r.
lsoorts4losthestibroatiato and ditnethylicanth
,horuptitfuns Pirsod-

ssinsiRse-110 ykltl. ot g1d.mmoodlos all ZO-l" (hison
'
=
i

0

tMuml ("not
"I p
lle
"; IICO. It wess u4iteal that sitnth
Itust"Inor methytostes much mewtv readily too culTritic than 'lee
.1~4 the voyntlortic siatithine. G. M. K~slalxwtl
00
:
AS4.lLA NITALLWHOCAL LffE2ATWg CLAUMPKATON
00
Ise. *#am vm&nv
Wee

11411148o wiii, o"T Got 4
1 43LA" a" SAARI cm a" Ali Ise.
U 0 AT $0 AS zzA4AA1 Sued 0 'S I IS a 9 M a 3 St T
to All IF9 it 11, a, an a, - voluoval v1
0 0 0 0 0 0 0 0 0 0
1
9 0 0 9 0 SIR 0 0 All 0 0 0 0 0 0 0 0 0 0 0 0 0

0
00 A
A Dirsivativesafsuffaasslaide. Ill. M.V.Rts 401d
M -I it 111010 W) . ps- roaster, M.
$$$ -
011
24
7 O
U
.W
V~ M. Fe,loattiva. J. Cris, CArso. IU.S.S.10 I
1
f
A tmw
1
M.
ACOH) (30). ji-I er, an, 19
%
-2-
IIII
CIN
UJI1011119
l
IV
" swr
rV
I"W or
U
~ no. o
W-
(194 4) (LaiglbJs %alitrattiary); cf. C., . 33, 24. l - -
C
)
r
,
.
Y
J
"
*
opplified vullanilAntigitni were piepil. and, tested against
...... 1. es I soil treated with I ty
in SO jr. PhOll was brilted to 135
4p 0 a strcliux-mci and paleuissocoaxi. All were Inactive against Nits, cosaleal. trarviell with J%lr?CO, fillmd anti treattil

, thelatirr: tile activity agaillst the f0firstar is given as% with M011-11C, said tile sclul. IICI Wt isputrAlUrst
00 -ad the istivity of sulfastilartilde (bi parenthtses after tar 16 yield owe. h, 1XV. tit. W.
0 atysithetw-hala). (log.) 6-Methatrzy-2-chkarraquJimlitie (17 C.) sand 40 C. AcNits
'
V* f
f
d
2 f
laild 7.4 e, it) xavc l4setkYlamixa-4- or
irs. with
irs. an
2A
for 4
were heated to 180
0 (pis. old in ideph'as tit 01J.'stamijo) Pf Pit" Joe. fit, 1=1" which irtutisehl with poerniaN11,; no reaction omffard; after
d
f
f
0 a with hyth"lYstal iiY litaling will) ssq~ 1-1011.11V1 W lhz
0 si
ilts, o
or
I[.? S. CUCI And raoillimalloo I)( the reactioril
-
12 bri
a tIlliP there "A. talastittv.1 41
7.
at-metkaz
7
-
5
I
i
it (5
)
F"
011)
W
C
( .
.
.
it,
y
samintsquisroline
tit. tell* (hom viultr)i 4 a
of thtt arnit
.
.
a
0.
loan
1
yv
a
).
(
(
forratell %lilt 111.0 K. I Its 61) cc. "Mier cotils. 7,7 g. 'NiarCO. .
.
6.4 g. p-AeVIICslljS(hCl (1) Ili llysWille Salve after 3 Its%.

0g gs, Ill,, at Mp-satoldmid
"1
which it. lipli.slyord a* 41,:;Vr I,, give liallandtillyrixt.
,
"step-
Oll
ti
l
ti
lict rin4ism. in. 20-0 (froon
1% At-Oil), which was Alphas.
mi b
10% MaOll t
so 0 -
le
t
%ayar
(0); Istratilivot "li
j
an. iM
2'
1104411' (frotal water) (35)
r
t
10
0 o
y
y
-
line
as
8' Urtams b0% AcOll)
4-Aroltto
#I-itt~llwx
214
AD 0 13 .
,1-
e
, tit.
; free ea
. sit.
1
.-AeN1IC,J1..XIf, (S g.) Ili 35 cc. watef with 15 X- I Anti
il
id
J -
.
.
.
,
y
quis"ne (4 At.) and .1.4 g. I gave. as abovs, 2 4 X. 4-t
3.
00 , o)-
,;m
fag
0 S. Ndi1CO, Tirlded IZZ K. m.(n,tty?j3 tal. .

0: It airtaxilsdi, ras. V8.5 it' iftwit thl AcOH)- hydrolysis
ilh I-,-, Am Anti. m-(Iu1f4nda~tJ~)axtJ&e, m. 173'
,
di
% Oman water) which was hydrolyzed by 10% NaOll it#
4-sW4nikm~1"-mrh6xNw#n,4ixe, in. 274' (train UM
.
A
&A
i
ii
OH)
i
(71
i 11
7
I
1,3011) (wo). Tile Cotlesistan
ng p4prar~
01
(froal 1
' ara
ntiqu
sso
c
.
ne
.
gave
S.) ant
g.

0 j
(If
Wall Pfl.l. AllAkItIMAY; like Ar detir. t3j. 212-13 as, ZQ.:1 "
l

" 40% AMC). the frarar bait, by hydrolybis with 20% amidis.
wh.kh was hydrolyint lay I#% AM tit fi- sulfa ati
-
,
Naoll. tit. t5rl, (front W% U9011) (05). tdfasid-
'
110
l
I
l Re, tn.
iven'do
)'
added
O 2IM-10
(Irt"It 5071P MAIL Cou"satitt
with coolin
to 40
bratril to Itial
CLSWI

~ -
ant
~ . etio
;
dialidalithpM.4 we. l'Irlivi. It"gli
4n
ith
l
l
l
l
b
d F.
.
'
f
4 f g.
.
t
:
-i
t
f
lum
s
l
i
l
bl
l 10
6
W
at w
ro
ait,
ay
ay
AC irderjairdusle, tit. %M-V; free
p
1
1
m-
'4
log' (f
14011
th)% A
Oll) M ix
irs..
em -
i
i
ista
utri
oil
r
ea
. ant
et )
j.
rom
c
" ..
.
0%
-si
Isomer. Atilarrip., an. 216'. free base. by hydrolysis lilt with JA% N11,0171 at 3P xuvv

Its. 1951 (35). o4somer., At dtrir. its. 21V
)11); free base. an, 11W (20). 1 and
(train Act l
W* iftwit Witter). while Atili'littatlam ot %;Iffit"Utintlair lilt
N11.011 gave NI-lialfame
amide, in. 219' Ituin A)7-9 EtOll), anti the U~t
.
.dk
anthinnific 611-lit Save tile -"( P-111W.II.C0,11 Save
deal ... '611% M011), which was hpistalyrril -indide, ni. 241' Oroni li.5% AcOll). Ctiontarin,ultonyl
r U101t.
AM M,ZW~rhl,stial, arid
1 s..4 .11 4-1. 41a9 141 UK a", All
U is A, W3 4_-F----1--1--T---r--r
0 Is to a K It It It It of
0
-
& gor 114000000006*04 00 0
000 0
- - 10 - 0 0 0 e -0--"o * 0 0 0. a 00 41
Ant %*two 01411101110"41
0 0 0 0 0 0 0 0 0 0 0 0 0 00 0
0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 e 0
.00
.00
40
ze
too
to 0
11101101
coo
jo 0
:0 0
0
to 0
1:190
too

W

00 00
0 N'soll In P-4miftod .,.,u map iffibifox - 00

00 m. A09' (frmn N)Tv HIM),". fS-Aminomunturin
'
(2
) wilh3
99
4
I in
f
CO
3 *0
.
.
*
.
r.
.
e4
gave
,3 g.
PkeNW(ulf-Istamid0commurix, m. XW* (fmin 75%Acoll).

0 which washyd"yxedwith 10%.V&Otl

pumar;m, m. 101' (fmn3 40% Is Oily the Id,f
00

00 tumixf. showni piond,ing witity a almi

90

0 0 0 0 0 0 0
0 0 a 0 00 0 0 0 0 0 -0 0 -0 0 0 as** 09 Re 9 0 0 0 0 a a

0600960006660906660900000*00 - 0000000000#0000
04009*0*0000*0009000 '00006060000000**0*60te
0000
C 9 IF f W A L a $1 0 PU 3: r it cm - a n
.a me L 01.114 ..6 .1. 4'. C, lot avowo's :1
0019
1""lirmalsli'll almawasul 1-31-isnilyll. v I
0 o;;
OOS
sow
00--
11 9"1 OW it 00
w33oq-qAqdwss put I-oMw"ua'-"d4W
1 00
003
so= 00
=02 Put
ic. 00
A as"
ju
00
00
im~ 'A
Put .03dww
00, 00
upvwvbo3 pus
90
00. -L" *#t'M
00. 00
00, 00
00
oe. 0*
00
0 0
00
W"r 8-6 a m 3) -1-,1 V- 5-7-9-y-r-T-T
goo' 40,40"

04; 4
IGO
of
a it M 0 Is 2 36 V a it a of a 41 Ill 6

so
As: to,,
00 All I'mmi R- Clwiso. "I wills M41wri'l

A
'i '
00 were pfrpd. for
011011M ,

yrihnsr, b, 191-41% mV
'

*
so IX T. 411
;; 1., in. Its the l-reptil, J
UVAJ (M. W-2.7%
(Of WA
Wurt, 61111 At X)-A
Milli MA W. 'tillallihimirill I 44r V
yield), I M imill, tit the wa heated Ill linc

11141 molled too
00 Ill %%illl "Jill ;,C. hill filti .

there VIVIIII nuffbil-ralAr Forpla(Vulesal fill IN Phs grtiop fly

~Pke"Y'amin")q"'N'
00 8 )orhl M-3 so. -mic 2-ethazycirwhist
lito (furntostion Lif ZW.S Is. I unie
"
414W-110 its: N-31i"K ILA 9- ttw 176Y bar*, "1
tktaiswd by mvitimil;
00 )
th'
VIIIII
field (V)).
"n
,
SAN
.3
with the t1woretkal ount. sit hift
NarCf)a
1 1 with ac
0 m. . 41.7% (rcidion heated 19 he%.. vIA. of

b
t.
,
0
0 in &011 nn a itawr bath for 415 mitt. gave 1221 Is. of the enzene twkv the usustl).
INP-00
oxedviorisolitw (VA in
41
(rewtion inixt
0 *
--jrrt-~I*,,udjljC mrtksusafale, tit. '2`76-7', off which 9 S.
itriolinc Urfv added low Is; g. 11111 '
of
3
I If)
i
l .
.
.
a
heated 24 hm., 3 times the tiquil vol. of benzetw); 4.
*
t, ql~
All'
f
0 .
p
l
alill Illized with Atesco
".&41
t (,w W4
I
tM t '-4
,v%-ryhswyi4I. .1-Norts'amitro-
isomer, no, =
..
i
.
wa
00 1 4,"y1p4evykswiR0-?-
1" yi.Ll X.M It.
' (VI) (MACIII)II Illitt. heated IN h1ol. in 3
linsirs the usuld vul. of benzene) results In M crude

(,lecompts
-r. its. J.
*0 7 yol- 1~& 3111
p-Ac -ClItC01ort. awl
(xii x.). :;:A) It. A,
yricid; it was antarx"t &L's the xgaAY&-biS1z-* I.

.
o
&
~j
!~
y
11
6S) I.-Alroll wrte licat"I ftlor 4 br*. to yield "67. Fj
J I-M
wairl, with I truil. 11,0. in. I
vj
Ij
Ph
. '
with Ac
0fiw5hrs
VI`- UltheN-Acdoior
ivm
Alloll

I
9
I - 'i~rl for a total
Xi-.
i1mfill
vaWlim licat"I to'
7M
) i .
,
,X
-
.
with I Witt. 1100.
'
-
1l
X.
K.
If
c,x)kl to) 1:311 arml filteml gave 9,276 6.
t
( 12 mill 1". 120-W
(ticconspit.). Us. 2-etholoycinchossinoylacetatc
*A
.,
a light grey postorder (5.75 C.) In 25 nd. CIICII. treated at rourn temp. with

3.2 It. He in 21) nil. ClICIs
the "vent evotpol. an the tessin
1 ~jl it hich .,-WeareNtly h,-jt"l will, 175 9. Pocto .
bath. and the residue stirml with 1W nil. 10% Ifflor act the
meam both for 15 onin.. givr SklUip,.
'llromocifetic "id (VII)
161-V (urictir
tit
I
VII il
)

V"" .
.
l
,
It.
;
' W sid. 4S0' Iffir. rriluilml 10 fill"-. giveil ().-#J C. ?-kjs&0r
-m.); otberatterul
(unc
J. A ASTAILLIVACICAL LOIE*AfL*t CLASAWICATICIN I
1110-1
likill ON j.. is -I

-
ff It it to 0 K a It III K I It K An a S a nor 0 of a -1 x IN a
1 V

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re 0
go
go
CO
0
see
11111104111
wee

0 0 0
A A
9 1 1
A . - it
SO I -. ,
0 0.
00 0-WE110KY-4-Chloroquinotine, %I Rulasov Alld ;-00
M. V. Lisguntiva. U.S.S.R. 64,r~
00
00
acid
00 IC is 1r-hic"I from p.
anisidine and oxalacrtic acid by the Wi4icrmis rrartims
00 fliff- IrAq. :1:1191. 'rb,- acid i. deon.0h.syl,st-I and th,
fill zirtnii, k rrod-oor-l bv CI, Nt 11~11
00
00 ISO
-00
046 C Is Tie 0
00 11=00
00 0 o
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100'
SO,
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00
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fj
41m~%Lx tTALtMICAL LITIVATI.Ift CLASIWKAtIC* we
Ir
00
'IN. U.C *~tsll V%v ksi
-IF
~-u
It AT
0 0 Ogg 04=jffmjwla
0
4
0 0 41 0 0 o1 a m w N IL a x x x I IV Iff

As
0
0
e
9
0 p 1
1
1 l
l rr 0 11 At Is Is a it a a
1
1
.
70

~A I p u ... st
A
"
.

4
0
i
At buty0iminotJ alpylquinotino- M. V, Itaililvoy and
-
P. Arrmlaruk (Mito,try of fleiltif.
A J. den.
CAe
16
m.
.
"
chloroquinaldine
D (*-'t) S.) anti 3N) tv. 33-9 N&IISL%,
heated to gentle boiling fur 1.5 Isrs. anti allowed to stand
. h
IOTMIS t. yielded X's
jwhich was converted to 22 g. free "id (13). in. Mored Impurifin. linted to boiling. 2nd treatird with #o
(dec%suipts.), by treatment with IICI; the acid is fairly N11.011, yielded 4.7 1. crude V. in. IW-2% Imirified by
go ,
;~j vlol. in hill %Alri. hot HIM, aluto%t Insol. In cold water, soln. in dry Me'CO, fiddil. tit t lie eali-it. sulit. of Ire. I ICI. -06
st
go !:f iMr,co. and Md E'tOlf: the air-dried acid is a daydral. amt difit. by Nfr,CO. the IICI -u11 was then ctilviRtted
I**
-~ twhich hvws water at IM". 11 U~ lr.~, heated with 30 c. crIventionally to V.
'
~1 .
040 8
for
Ilsif in the prewistr of a little piptindine to 175-M
J 00
V
Z 4 h 5.d K. 6-mdkory-!-ityryi-4-juixoiixnulfoxic
a60
m. up to 34.3"; Na x4ft white
'3 rimil" Oroos water?. olooltrately liol. in water, 11101f. =so
goo 1%tesCO. hisol. tit Hitt). 111 (4.5 g.). 0 jr. I Alitt hylamitio-
*
i~ Coo
) and 9 cc. water were heated to 140
4-tirisint"ritane (
0 for th) dild. with .50 cc. water. extl. with Elio. and COO
go, jthe ext.steamAW,L; cxtn. of the rr,idur with Et.0 and
coo
- ;(trying with K,CO%. followed by rvapn. of the solvent,
4
00 vAn. In %te,CO. and Irratinent with the calcd. amt. of alc
4 IICI 1 11 1 0.7 C. 6-,ndhoxy-4-j(4-die1Ay1amin*-1-
ol -Z -
1tyr
uixotint -:110
VWW
in
l
4497--i

9
V .
.
n
if ".
.
, Y
y
q
'

~
l (decompri.)(from rtOlt-NiesCO); free barit M,
245

-
,
AT
t colorless, in. 124.5-5* (from li"n). 1 (14 g.) and 21

"
,
I-
".I
4.
'
l
001 C. M, heatM to 11IS-:51N)
(or 5 firs., dissolved in 2
1
-td
a
e
ith StO
d
KOII
h Mc
CI
d
i
1
7V, .
. w
n
r
w
t
, treate
. c
II
,
c
ga%-r 11) S. 6-,ndA,,xy-4-j(4-JietAyI-
igroin
crrtd. from I

1
"""' ,
vj (VI). m. 12d-7'.
.
. I
.
0
d '
:
e h
ted
4)
idi
Bill
I
i
I
1 newer
(
ea
.
2
ller
. sli
(O-t) 1
-g.
ropi p
..
I
v .. .
1-V
2to 1"R~W few 4 he%., stramAktd.. treated with 11 cc.

i
" coned. IICI anti 20 vc. 11,0, heated to 0045". dild. with s 0

O's 150 cc. water, mind the insprtinatant liquid drevinted (runs 1:14 0
~bSjqjJWjar-Tftc
low ba~'Av
71#
' i -T F-11 -1
.
MI L S 5 FW

w
1 2 a a 3 a I
"
ua Aw PO LS
p p tr lip CIP K Is It it It It a it it of Plus A I U Ann
I
6 0909 o 00 0 0 0 0 *000 0 0 0 0 0 so 0 0 0
a
l
4 -
e 00 0 0

-
es 9
s
. IS I to 11 12 If )d Is 16 V to
1
d
a 34' b' 26 V As 13 14 a I$ V a 0 a 44 a a Is
'
"
1
~A a R IF t . I IS L p a I I T_U_V_V L I AOL N.CC W a IS li f
'1:A1 IV
11) (0-1)
A
) ill
11
0 with d
1 (1j g
Synthesis of derivatives of as
!~n .
-
.
.
.
.
1

-line its HIO "-. Smostirr Slav, IS X.':
.4Wd""`V' 'Y J.-A..tv
treatingn
I of tuberculosis. L M.
R.W. lm,.'
Y
.
_
221-
is Ifealth, Nfascior). J. Ceis. CAelm- (IT.SS.R.) 16 mmilit. II&I-111P. ill,-tit
,
0e ANOW).
-A wile, of naplithoiluiesome desliv~. silsolvemS 1. Noll) (0'5j~ 0 lit.101ij-421ilinc JA%C
1

have is definite I%-. ellret its aviass tulwml.44 in white oil.
,

Illice. are dk~iili,A ithe USIciance ll~s of the comilwts. MOM (11.41. Frosts 4.1 is. I in.
4411 Sv. 11.0 At 7W fle.61.1
-
;
-09

arc given its lkircit
0 1IIVU~ A76 ISIS. licr I g. lumly wt. ftr of 14011.
a.

0 attawr A d,tv Im L' -14v%). S4 1.2-naphtlN.juitume-4-
v_V-1.
III jr.

asil"11,61, 11) 1 It, St.) I.$ cv. wAIrr, trmtc%l at 00 with tit. II'V AIMS-
0 a
vil 4 1. I'hCIItNIIs and "I g. AcOll in ec. list), stimil at ficaltion wish AkOll of the ISIS% -Naull subs.) (0.0; with
'
"
N
l
j
h

0 An: ~I* hit, '1 1 fir., And let b M'd at 0' torwv" hrs., yiettlel
' 'oxv-N-(~
-Call"
t
s, Z-hY
-ff4p4j
VI) -1. fl-m4phsho, Nino-
mimine
resulted
) itiWoler
I 113 x 0
;2-kydro..~-,%
-bexzyt-1.4.osaphik,-quixoximine, In. 1,C1_4.
1
l
0 .
,
.
.
water added to 5.7 Is. *-I-utitititi-i-itietliyltlli;ui4e ill L'dl
0
.
(front EtOll) 0.91). P-.NI"NCJI.Cll:Nl
h (4AS g.
)
t CC. watts still ullowA.41 to mand tivernight Save
wt M'idi-
in 50 ce. Ittoll. inixot with a boiling sWn. ( S.r
00 X g. I in .
.
kation fly AcOll arist jmriti4~mtmo through I.- NA Mit

.50 vc. IlrO, Im"Irtl O.ip hr.9 dild. with water. still riagetf,
'
~
0 .

3
-hydrovy..%
gave 3.7 x. vtnde ;
.pkorxvl-1,4.xapht"mimox-
-
'OV
i
d
f
i imillie, not tit. Sip tit T.15' it e G7
m
xe, tit. Z
a
ranupoij:
ter crystn. from EtOll, in.
(
00
258-61" Mccninjut.) M_"). 1 (13 K-) in Wit) cc. water, g.) anti 2 g. N3011 in 711 tv. w4trr at U)". trustol with I
019 -3 treafetl at IVV ith 8.1; It. bulfanifainide in 1.50 cc. water (11.) Saint. given) in 2.01 ce. Wat". filtVfC11, All'i W1.11161f
'
,

so yirld"I S.
with Acolf at 70
. Slave 1A K.
'
l

Atiyusmonts"sne (crude, tit. 267 Smarificil fly %4n. Its.
I'lifil
i"I throogh III,
*
1
-
0
N
1
)
0
i
0 0 ns.*%~;, Nj~Coj. whitt. of F1011. all,[ plotti. white warin with

' a t
cr
v.
t,
.0. I
.ttmS,at. if Ln 9. 1 in .
0
l CC. I%Atlr
(
at do" with stirring over a lwri,.i of 0
5 fir
-ith I
,
see
1.1mompli.) (O.trz). I (III ff.) in -T-15 cc-
A A01111, in. 277 .
.
,
K.

If,() a, 74to witis ~~ IS. p-nits-Snifinc in I.-A] m. FtOll praw Qe 0
filtratiort CAve K.
A...,M
-
'-44 V (11 Ar.-nilic mi,I (10.9 it.)
' -
U
5
1 (13
i
(0
IT., t
C. X N44111. tr~atcd ith 13 X. I ill :00 cc. 11,0.
SN h
tV. WAICr (MAtc-I With Ill 9. 1-
.
x.) In :
). see
IICAtV1I 911 75% fillCrell. Anti arislificil to Congo red by dil. Wilincluntipyrille in 110) re. water anti allotted to '11311.1 I"r
--4 IICI. KA C. J1 12 first. y"Iell. no ml,hi. of :Nlt) ce. lio- ~ Na'CO'. I I jr. to 0
betzenearitimic arsd trtrahydral;, doc-st riot its. 303* (0.5).
U! '
k-
i-X
-Io
220, F
5-diat
vr
e
ooi
tk
O114
l

1 (13 X.) its cc. %iAScr treatetl at tW.* with 7 2 c P_
: is~
e
ff
' '
c
t
.1 I
l"
j
p
y
i
fi
i
,- It
EtOCJ 1, XI I C.Nlv: C I I C(.h Et in I I M) cc. FtOll yid,f,,j -
(0.00; ac
l
calion -ith AcOll Ktv, the in
'
'
'
: 9

kydroxy -V - t p - efh,, r v I ~
pkrm.W) - 1, 4 - "a pk:kNu I propi fill in e. f.
0mmulm.). I
r,..t 13 K. I ill
:t
wl y. i-Mrs, frvmt'l
7
ith 15
N
;rot
i

o 0
dcc-tip. =-,' (from Acf)l 0 tif..O. U-4 0-I(P-ttictlumy. w
.
. X.
A
t1
m. -'1'r
anti allowt'l to stand f.-r 12 It
I IA
300
'
All iliIIII)VIrotmiat r I, alm.vc gavc '-hydroxY-N-(P-m'h"'Y.:: ".
-
Iti (fnxn 0
1 ..a IS Ant Sandi) 10
uTj IV M3 It of it It u it Of 9
1 0 it CS, OC K a
0 0 0 0 a 0 00 10 a 0 0 0 0
0

a
0
:
: 0
0 0 a
0 0 0 0 e 0 o 0 0 o 0 0
: 0

0WT
00 A
00
0
0
00
00 a
0 A
0
00
00
0
0
0
a it 11 U 0 a
I _A_rt I L L U- V IF I I
JAI
-211C "R! ...' ..-. -.1
VGI~Cfllffl A.0 PRCPC*lltt WD1.
a At a As 0 A
IV. ),1, 110 $411 M. MIA)* Ortnts E*1011-MrIC11). The kell"Ir
Synthesis of Z-quinudid -pyridyleju
'114 lifisol.
(3.17 1.) in 1:11cc. Ur~ Iffir at 50*wai treated with 1.1.4
NICKVIN),
concill
V.-Rulasov'Mirdstry I 110211h.
J. rrX.
Ch*.i. (U.S.S.R,) 16, 461-70(tilld); cf. C.A. 39. M1.1- fir in 21) cc. V4416 Illir ami ficatni to W)* 15 inin..
was prepd. by ix WSCUO and trrAtCJ with abs. L1011-Me.C0 to yield
2 v-Ariants: I0 f. 4-pik-ofine and & g. ZnCls were heated go% 2.(#- i1wridr)-t-brompethyl 4-Prid kdow-211fir,
decamp. 1 7, tit s (3.43 g.) lit .141 cc. Cifel, was added to
lit fir%. at M-S , dis4oli-rd in 33 cc. 10%, IICI. filtered, 3.78 g. NallCOs in 45 cc. water and shaken 2-5 hri.. when
diki. wit h 'P 0) cc. wattr, treated wit Is charcoid anti fract
titmally pptd. with 151"', NA.Coi to Yi-id the nil went into soln., after which the Asking was continued
1.5 lit%. to yield, froin the CIICIs cit., 65.57p 2-joinnelidyt,
product. in, Ifli-S'; the 2nd variant was: 10 g. 4-picollim
and 35 Z. BuOAc w-m treated with IS g. chloraland heated, 4-pyridyl ketone, in. 117-18' (from par. ether); di-HCI
salt in. 221-V (tictompo.) (from Htoll-McCO). i
to 1:0-5* 9 firs. to yield 42.0% of the product, in. 100-3*.
Treatment of this with ate. KOII gave 00.5% -pyridixt- flyd ti to of this in N IICI over I'd gave quivaclidyi-
.4 idraby:ol (rarrm.di .1), tn. 57-S' (from pets. etber)
u: ~43* (decottipti.); the reducti-in of its ozakile an. 174-3*); the mother
arid, sit. 60* gave 60R17
IICI salt in FtOlf over Pt oxide at 4-Pj'r'- liquor from the isotation of racrtnate A Isydrachlbride
dintpropionicat", tit. 2312* (front water); If $aft in.
acrylic arid (M) c.) wartned with 1170 gave, an neutralization and evapti.. 0.111 g. of raermak 8,
Ide.
IICI give the FJ rster 110 salt, in. WI-2' (81 fn. 15", (frout Melco); ds-110 S.111 tit. ttr.-Q*.
.3% row it the kctoac Is redumf by hc2ting with (Ub-Pr0)*AJ In
i eittr tit. 67-9') (Ittvin pelt. ether); reduction of the icl iso.IWII at UU* five 2t) ht%. there results only the racemstr
f salt as abivc ovt-r Pt oxide gave EJ 4-Piftridineptropionato
UM jail tit. 114 * (front xylene)) when the r luction Wit A, Identified by its ut.p. and that of Its IICI wilt. When
ruUI0hrs.st'2h)'inRt0II. This(0.64X.) e( citha raccautte is boded with 5070 AcOll in the presence
in 30 cc. water
was treated with 8.2 g. %*&OAc and 1.6 g. NaC03 followed of NaOAc there Is formed in good yield attly 2-(4-piperi-
by5.l X. B&CI to yield FJ X-&Fi.-o~d-4'P1'P-id1XeProP% .-fr,
ToNa0lit(ftom2.4 Cf. Nall In HIP dYI)dA, 4-prid~pf kdont. which was [a-"ted 43 the IIC
there wits ad&st 17 g. of the above and 13 jr. fit isonk-u- salt, itent", with the above prepti. The -' racrinste,
timite and the initit. was stirred at ff)*, 4 hri. to yield reprcstut the 4 pu-ibic sturcuim)nim of the quin"OPirl-
5R.4% crude keto ester, which was boded 3.3 bri. with p My1cstbinol and are flit 2 ditAtereoismiteric taivInAles
17% IICI to yield 91% 344-Pipwridylethyl) 4-Pridy(
kem in. 4 1 exabite in. 110-5-1 (frotti Rt01 di.
-00
-00
-00
*00
moo
to 0
coo
zoo
asell
1`0010
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200
tse 0
moo
MMKI;
'.FTALt'--v.GKAL tiTfINAT6011 CLA%IIFW-AT�Ck 9-z-
z
;At WL.
L- T-T-T -7 11 A 1 5 A I !A An j. s it w a n a i sr ei o a a 3 s v
it It p OC Is ff 91 a K a C9 It
PTO 0- 0- 'or : " " 0-re;O-0-1:00000411100000000006 0
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- . I . . . . - - -.,- r, . - - - - - - - - - - - - to
, 000906 94111 $0000 111111111111t
A III M, is n a 36 is 16 b a 24 1 is )I u :3 is 36 lop 1111)04111 11 Alume"Ce
A I_r__G is a II. L_ L X. W.,76, W-A 4-1-- I_
A
0 1 its I W
4,141"Itit of oniffill4bil 1,11 dillf., lot, V If-Jo
I.Alts. ri-oii.64i F
R , I., jvlt~ if 191111 N so IA
I Wn$, Ktfe prelill. and foulod imtettvC
00 17.11;11t~JjUjwk TrI41MM ift aVUn e%l)t%
In the
prepri. '-f. file 4.h3t(1jly6Iinr%, hydrisly-sk to( 4-pyTidyl-
09
pyti'liltimn fill tMe [flit thoill III an't C614N). fi,llowrd
I's, I'vAlls"Its .,I tjor 1-111tilng I br.h.-wirl Of,--- .$1t8
Wit
v 11, 1.1, kit Ou. 11010VA. ~Ltgw, -goo
Is.
*.'.6 I's, b Imr,
R ... h-o oil *it is tilt% -tuh,u~-r kit-fit C(s, ~v,,Iugttwu
vo,s-l; the 4-441 omi-, Itratrof viiih IIAI cc. 11,0 aml
Iturt%k4l. I.W.1 .141 filill.. filti-red. and Cyalki. to llrynktv4,
00 gave Its,; tit, tov. rhi, (12.6 K.)
11.1 51P it. Mods %vir - fivAted ,it 't Water Is,111% 3 11"'..
tv
00 % Im
-11 file %v%- VOct. %V.%, milimmi ill I'll 40, :111.1 tilt- Z
mmdn, Iti.t. miwiril with 1111111 ov, Nsp;. NaMl mW -tvarit. 0
00
09 tit.- N.Oll inij r%1,1. with (Im's I Is,, I if I ll%'l w1... 1. -11-4 ..,h M- -C* 1,
I. tit 1.,% 1. 1.), W. ,-. 1117 1/ .. ..... it,., ti ... 1 .4 M.. .%-- tilt omn, I's
.; tfir I% k, If.,.0,A .elh -I %, 1- q
00 0) 1_Av:l I I mad 11'Ni'll" .1i't it. .. tit. so
. _4 isvir it-Ilutitil 5 Itivit Imst"I sigh ., 41" N.0 M MI'll Ald. VIIIIIA thir
bill' 11,41 -11111 13 K. 141"t- S3011, And the e%C"!4 114111inc "k. oil di'911. Kave 2 If. "! ZVI 0
remos,rd with w(cmit: the residue. treated with 30ce, inow)Pyridsme. b, dijp4rale in. tilt' (front I-go
M111"O. 1 (7 K.) ~klld LN K. IIINCIING-Cli'ClIONI't, Wit"
Ill", N.&Oll and ei(d. %owith j:ive at-Kit t.5 g. 4-
re 20
1." 1411 tit. INS'. and rw X, W-Ind'. fluxed A tit-.; fmaittictif jill 1411; N%toll di"I riltjt~
0., it I'mO 4 41 tilt RIO ItA%-e ~A it, ttut, a
too
I". %t;g to, wild. 1. 1. 17 9 lot 11
...... I t-, X.; 'In't 2S if, Fitwil,vil. 14 111% m,-, It's.
It .... t A,-01 It.
tj it it, I
i"li it. 44. 1; 1
V.- __W-_W-W i-
A t I, of~ v in .1 A3 a 3
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.A -A-J-A~ -0-ILY-2-11M ft V I T 2 M a re use
00 a
I.."c4tift A^41 PAPI)OW4% self.
Derivatives of p sullantylphinsylglyclsees. V M "I" AJO .1' all -00
'Ir It'
-::iis I ; V-Pyridylamide (from tile Sir "ter.
:o i7k~~s~ (USS.R.) 16, POI6-70(ifl-16). cf. C-4. aft" 4 Is". at lml*). (frofif :NIP',
*0 r i;f 40. IMMI-A no. of derivs. of N-(jt-stdf;unyIphenyI)- PhOlUrCONIf, (13 X.) Rull X-ft -Ifittlilmn4l, h,.,,,1
I jjj glycine (1) were Perelifl. for medicinal! evaluations against l7li-M* 2 Isev., ervaed. anti trrAtc%f with Il'o. Itavr
~111 %ff% Xneiltyrur need fultemulcmis. F-uperificAtion or mitildix- . -(Il-SO101 WY(a I ~S-Ph,x V1.1, Me . vle. Fit, 210, (fr.,!,o
i'l thin rmidivil lit Pharply drerra-d bi,J. derlirtlye litsit gas Pill 11). A %oiltrit,imt of `
.1 C~ lll�Clt(,Nll,)C(hlt fit
rogre-sr; aphisibercular act" MIS weak in all Instances. 23 tv. dry Isyd-lille. 11-r-Alell with Mirrinst with 4 it. p-
nwMe eAter. V-pyridylamitle, and thranilide wrrv r-quiv. ArNlIC.IloStitCl. tireefl few I br., ht~ate,l to -if*, At,.l
to tile free Acid fil tectewlytiv (~ts. I M3 it.) lifitilrd ititil %-alrr, yiddr.l cry%t.
ill. irraleel with IIIR ji, roncil. If#80. X.), which, I%Iirr
z and IN) ff. Me(
j!: heated 11) 61111111 Ill Intel,, yirl'b4l. aft" 4 I%F-. itallifills vimflills with water "ind -11yii S, W;14 )lyilrtjlyinl by
'; set the owt-r3pludifig .110, ester, lit. IXI* (Irtotil litil 211% NaOll 41 KrIttle rtillil for 3 lkl,.: acidificitlioll With
06 " W ~- 40
, . 14. ateT) -. A 2nd variant wws. 23 #. I and 10A r. sueda ast ArOll gave drid. IIINX4111-
1 ~ ." jet 1,%) cc. IfjO, treated at WO with Ill z. Mirm S0sNIICf(PhC0,If, which tiorsnot ill. Uptes3511'(purifiril
go :1 it".. aml snove 77.91~- Me "ter. In. )$I,. The and plan.1strAvOll). 0
Fj evirr. in. 14.1~6' ((met w4% 1"1%1. lit PAtechiestisese o( this sultanation Of arm,ti, Minn. 11,
--I #w; yiaj t.V.x.h1�K I.. tile Ist variant. I*r ester, V 0
M-Sulfavation at filevalod temperatures with inillulk scid.
00 13W (front ll'tek. 1wrl"I. ifs &V~e Y*111 by the Ist r4rialst. Fificst R. AlexAnder Weliv. tI( 111141"i., I'll-W. J. A-
tin filerr, its. 118' (from UP), in 54% Ykid; Phteleth Oww. Soc- 69, cf. V..4. 40, 4,111.11.
ester, in. t-.5' (front N117" Eton). 71 A Study Of the infi-Aente of 11,S0. nes tile vidbalati.,j,
0 A10 h
brated in 114, re. N11,011 on ameam bath 6 hrs. in a I"Ift anti PIIN.Mv, at 14t)- Anil 1,R3- htj sh,jecre th,tt.
A: 0 400
~emnt -4 XI I.. savir, off cmiling, 15%1~e n( the eorr"llond- Ill spite of I c shad fell y 44 the stArti,is lij.jjrrLs6. tile A:,," -
belt ftae, ill. 2Ar%-4* It"- 11,011. The tin "ter 1.4 wact.o.s.an't tisc 1--- Ill, Ill"11.6. 4111114111
aft-1 7 lg. be.&IM tot VW 2 he*.. and Ille r~A~--, At 1,4:- . .11-k ill,
mwtwn i~ e.aried ,fit In numo. th~ t.f,- .4 i, --
too
1from 11911). The Me mter (5 x.). hentel with 5 g. cma,,,l ill tile C.L,~! tf 1,11NII: a-( in the caw if(
PhNil, 2 hn. at 141'. t"4 1,
ed, and nil elf with 5 cc. 1770 j1bX.NItj by tile adtb). .-.c-* 11,14),. At 110', when
JICI. gave a.dide, in. 20,5* (front J1WC EtOll); tile lVaction i~ V-ttriol title ill ~1 4 1,,Krtl tile rate of
too
IF
1, L A tIhtLUF4kAL j4jjSAT%.dil Ct4jStfjC&M*
Uo a
U it AV' to 11 rw 0
isp "01110 Cieder Kit qrste of st rl it KW I I- A I V 9 9 1 0 be 9 A2 a 3 V V
0 * 0 0:0 0 0 0 0 tt 0 0 0 6 a 0 0 0 40 0 90 :41 4111go* IP 0 0 0 0 41 0 0 0 it 00901
to 0 0 o o 0 O's 0 o o a 0 0 a o eip * 0 0 C 0 0 f 0 0 0 409
0 US, is 0 0 j

..990990986 -9-9-m--W --- - - - - -
*
0 ** *so* o *4 off 066409e000009 0

.01.1. 4f, I" I, oll.m I lie of
00 - tif [Its -N It, lift-,4 to Ill. 11 If., 0"1 vtto6 00
.
%0,1, It ov mitt'golhir j1 11 1 If,-

00

00
00
410

00

00 00
00

90

010

0 0 0 0 0 0 0 0 a 0 0 0 Wo 0

31 1 1 1 4 1 4 1 it 11 is m is Is it to to is v it Is 11 a
A A C
0f-%
.&.C1111I A,* Oxc#qml~ts -bt-
ifiyismtno-,
Plepiustion of 6-mathoxy4 e
butylamlao)quinotine, -00
0* 1). Stinnown (All Errilhii Chern. llmms, Re-imh
ljj~t_ %Irmow). J. (,-eor. Christ. 16, IM7.' 1;
i 19M).-Tvitts methods were cxpl(m] for thr iymh"ii fit
0 the 4-iinoter of platmochin. O-Polethazy-l-chlorotputis).
linr-IICI (17.3 g.) tutil 34 g. freshly oli~td. 111:011, Iscaittl
to gristle boiling 0.1i hr.. ri"M to 1191'. asiol pitittvil ioto -00
re. yieloh"I
III ,,, -90
00 r1m (16 st.) and Us x. -00
to. sg~,itlv rvilis% it hm, mi-I the iv,iduA od
00 X.
age
00 5 inkrif with Sof rc- 5'~~ Ael'M. vichfint 4 K. -t.wti,ig 11,0,FIA
Ouil.) mid the AvOll -,Ill wish k0111 f-m 1A x to. rv o
00
'00
AD, m, (fruits Nle:Co).
iml -,(N1 iv. 411", Nall$Oj, 1.)il-l mitil
0: (711 g.)
0 -ola. took 1)1;icv falmut. 2..$ lirs.) autt tmitil, Yk Idol N's G-
RD*
00 a which wav di,-A,IvnI ~i 714t
coo
cc. wiLrut HiO. filtrrtd, and acidirmf fit Cimigo reil staft
6-nwhoxy-4-
IICI; aftcr %tanding for 10-12 hr
"Flik 10;
arid, sit. -*qll*, was obt.tinvil.
9.), IT-0 C. 1, Will 13:1 It, 11,0, heated to 140 '=1 lirs..
'00 ~EOO
I cc. 11.0, ctx-ilvt to -10'. and thc mg.
itratol with 13'.
Lkyrr %cpd. and stvaln-fiWd., yiehl"I .1 rtblue if crull,
11, which, taken up in 1:10 IICI. stimit nith dia".%il.
d fil(cmi, and treard with N11,011, rave 500".' It. nj~ 121-
5. cry5til. from Nlr.co givvl pure It. us. Cv"t-
If z!
wrion of 11 to the 11L7 jalt is bcst done in dry Nlc~Cts Ivy tie
W11111. Of the thCOretkAl Atilt. Of ak. IICI: YiCllt~~O too
M.
too
U ig IV PO is t A To Is Aft 1 1 IW I It a I is DO -j A 0 31 1 V
~v TV 11 P It Cy M K Ct of 9 K ff Ct It 01 k1a Of # ) VA
O's
0 0 0 e 00 00 0 0 0 4111 0 0 0 00 log
0 0 0 ills 0 0 0 0 0 0 0 0 0 0 0 0 0 0 *"e 0 0 0 a 0 0 0 0 0 0 0 0 0 9 0 66,1/

Rubstcv, V. Doc Chem Sci
Dissc-rt.-, tion: "Itivestig2tion in the Fiald of Con,.;~Owids of the Alkaloid
T~,
10 jwrle 419
.-11-7,'nian 5-i Has inst irheni Ser.-o Ordzhonikidze.
So Vecheryava ,.oskva
Sum 71

Rubt-vatul A. P. ArentLruk- Amp, 0)4tkk,l Nk-
(19 it-1 afoot 'Itj if. Ft,%'CII".Cff
Nlt,).%14- III liraltA III for- I,, I!ks '.!1b) . '111.1
%till 15g, i-odwArt-
t I 10. :Pj g. liall, and I K, pilierillfir afirr 7 fir,. It 11.5
'013 gave toy p4trifivatitift with Ft~) and aq. 1ICI.
%tirryl notabir tot It. fit, PARAW ffrovitt twit. rth,r'.
~:4"IrA ;ttid 15 S. aff-r
_joill. J,y at 14 aft.r
'it
.hill. %still '-%of till. 1Q.). gave 9.5 K.
HAI). which -,Is ficating %$fill 11111 allif Ifilwri'lifir I.%,
A-ve) gavv, after r.-Im-Art) jourifirati-mi Ifir-ougli v%ti;
-ill, Ft'll0alul life; 11c1. _. g. Z-0yrylait'llac. Ill. Ill-l",
Or"'ll 1wir, ether). iu -I&1. ta ."tor :1 g. I-*I'()-jfI..I. It-
beflutilte jalt CA the %ague )10,95r. its, 121 -% ii--A-t I-
I~ lurm iftaldiffe sittli4fly Iravo, 3 K. r-l"M .. .... V
Ino inn- I - mrMythutyla wimp] quinishlinr. fit. 1:17
S 4 1 front) . I)icjlx;ivr t39
l(nnit 1-*tt)y. flyllngetiatwit J '_1 jr,
I Awl If Ojillill- I -iflet hylbij tyL,II)il ... ~ -2 - -tvr%-I,putwhr,,!
I fcl ,v,-r P4 ill 110) pvc 1-43 g.
#;' 11r,"is lot-t EN A"Modaz to(
;111 S. r. ether). 'I lie 0'.
'iftliI.IfIv. fit. W.V. 1, ffr or, rib.-ri
11111h d.1 Minot 4 - off. ill
room 1%-tr. rtli,rs.

RUBTSOVI M. V. I . . I ~ I . I I.I I

------------
RUBTSOVp MOV. .11 Feb 52
MR/Chemistry Pharmaceuticals
mThe Synthesis of,Quinuelidinecarboxylic Acid-(2)," M.V.,Rubtsov, M.L.
Dorokhova, All-Union Sci-Res Chemicopharmaceutical Inst im S. Ordzhonikidze
DAN SSSR) Vol 88, No 5, pp 843.98"
Worked out a simple 5-step synthesis for quinuclidinecarbo~ylic acid-(2)
starting with y-picoline and mesoxalic ester. Presented by Acad V.M.
Rodionov 28 Nov 52.
Source #264T26

unim
44
2

RUBTSOVt M. V-
Synthials of 0-istibstihited aithinriftysteri~
Inst.. 'Ninwom). 1111r.
(10111rUrt A h.
d. - 1.2-3g. No fit 21) tail. alt,;. HlOil wat
added 8.7 g CH.(CO.-M)t and 9.6 g. Ft 4-pyriclitunicrybuc.
and.the rnix*t. Ffirred I hr. at PA' and treatvil nith VVry dil.
bh(elhary-
ea rhosly,F)IIIrth III 4-P Im.t 173-5-1 (mottic &- ~ . 1 11 1 1
'I $(III( Lin. 121 -)' (from Etoll-Rtt:W. This
Couipit.).. HC U
i(4.4 0 refluxed 8 lint. with 44 nil. coned. 110 gave X( I-
:pyridyl)gfularic arid-11C, which, heated 3 firs. mith 35) "0.
0,-o a1c. 110, coned. its mcite. treated with K!C0j.n11d exid.
'with Et,O. 3idded 84.4% di-Et cstcr. N.e t4(;-S*. I mAnct-d
over Pt oxide lit EtOH to FJ
I
piperiWiteprispiOn4le, isolated ast the 11C1 S411 11). Q titffy-
like mass; the free base Is nutorphou%; Ircatumut with AcIO.
OW-7*
Igave the I-Ac deriv.. lt..~ - l1Urdm4,Ag.pvridine t
janalog) lit dry CHCIj treated over 8 firs. with 20A j. Br lit
CHCh. allowed to stand 12-14 first., conctf., lircated with.
RIO and KCO,. and extd. with Et~O yielded crude Fj
P - (bil(ethoxymrbonyl)brot~:omeiljylI - 4 - piperidbirpropionate,
Ghemical Abst. 'which, boiled 2 hrs. with 390 mt. pynditte. coned., and
Vol. 1,8 treated with 50% KC03 ga.~672% Ef 9,2-dicarbrikoxy-3-
Apr. 10, 1954 inuclUineacelate, N.,, I stirthiodide. :1.. 139-41*
M. EtOH-EtO). The ester rtfluxed 16 br3. rith concil.
Organic Cbe Listry HCI gave Z-mrboxy-J-quinudidineacaic -arid-11CI (M).
decorap. 253-4* (firont aq. Me.-CO); the pure product d,--
cam 254.-5* (from EtOH-1340). -This (OA g.) 1.1 g.
Agkand 8 .1. 11,0 hk. 2 I..:1dild.. heated to the b.p...,
filtered, satd. with HS, filtere-it, and evapd. eve 43S% V.
carboxy-3-quisturlidine=tk a&V. m. 265-7 sut STG%~
is obtained with ale. NH#. M(7g.)bmted with 100-1
ml. SOCIs 10 hr*. at 70'. freed of SOCI.. and the resulting
acyl cklm~HG UV) refluxed 3.hrs. with EtOH gavels
$2.7% di~-Fj 2-carboxy4t-quinuclidinea"fatc, list., M', D 7
6.
1.4797, (also obtained from III and 5% We. HCI refluxel
hrs.); methiodide, m. 140-1* (from Et0H-Etj0). Thei
ester (8.2 ff.) In Et,0 treated with 4.64 C. LLMH4 suspended'.
in Et.0, boiled I hr.. and treated with 9 mi - H,0 gave 88.7%,
,2-h~roxyrnetAyW2-hydrozycjhyr)quinudidiste. Iss., 15&-7*:
M saft, hygirsassuiple solid. The latter (.622 xj itt,dry
T
7,77", !.Y.

Cke", u
RMbL4ov and E.
_
X rn F slMon).
7777WI~~ -Wr -w4m, C.4; 48, 3978a
'77

77

qe,

I of ui 19 f I 'din M
t;n.
zhat. Obih kri
h h, -'4 4(joj ci- C., '24.-To 21A-3 9
1; rit. 1) i pr-1.1 Ily oxidation of 4-plcollud) in
v ~ a-
ILl !0 ml. -50170 NaHS0j, the mixt. cooled to
:,
I it i1 i umilt formed, t
- he liqtild was decautefl
.11 the olid iruw rubbt.-d with MI(, AcWhig 7,3 K.
.
vpnethauc, se (U) mixed with
C:Iism irmi HO gave nwiles of *JIN:CIL-
-W
CH ('jC11(OH)S(%-) CH:C1f (A), snl. itt hot H20, insol.
QC- -Ifcl give, after tile -U-Sull
in org. solvents, do--,s not m0t. A Rad 0 treated cifer-fra, m. 12"". Letthig 3.3 g, J.FICJ
.5tand 1 11-Lys
with 2.23 Q. X X"oll followed hy 60 mi. abs. EtOlf
'~
with 3.V3 U, CIIACO.J.-Ot. BJJ nit pYridinc
and :i
3 j"L
g,Lvt- regmcratrA It, which with NaIIS03 up-1--.11 ~
,
p1piriditit! juve. after illtratiot, 0
f Ilit pip1ji~Jitir III-1

gv-i~ A llr~+lug-tl ~tirrzng in PlAle of 3.1 g. It %vil!. ,
C.Valln. of tile flittatc -it -W i)V vicua, aila. with Etzo,
2-%~ g )i.NNIJC~jXI1.! in HO at 70-5* gave a grftrt
'[;; 14'
ti-
17'
:
id
E
Oll)
f !Ion, wa.,xhing the SoIll. vith, 15% X411CO" and (Ii'm . 0122%
-
en
j1pL fit-
(Mt- In 1.,
ront
t
.
( lj, tic)
fic:f I t.ho i, 1-16,*o IICI fosn~d a 911"' th"' 110 -11, ([mm FtOfl). I I v,
51)-' EtOH) Crodt, t; thc- Lt analog k~7ilit-d lir- i-jusly. M. K.
1w u,,i 5 1 It 15 w]. Hij 4nd 30 mi. ~0~'o
.4h-hpic otl,r, and after rivid
%hc -X1 Lroi g 1, 11. r,,pidly
(,~vmw v, Ir ni. 5S-44)'; 1 fort" a Hu
,d1 siblimc; M,,rucli f
losi of 140; it"! J,y SJlt, in. 159.5-61.6"
'

converted to tile Ilcinihy adni
-t1c4tc. Ife.
t
.1 Vgj
.
cll-.(0:4111~ nq 7.6 ;hLAcO1I;,Winiji`
gmife 'u,
7-

batc. (IL -~V ptivie, If in
-wnip. 213 ee!4ijilt,

%light ptevairc gasre 01% y 'Pitc,wine-
-
-
.
JI
l
O"
i
ldi
it
-
e-
e
v
alt. f
ng %v
UM
h &
t tile fat'
comp. 2i'M) 540*. The IICS sAt mflu.,ked 4 lira. with 4%

RTJBTSOV. M. V.
Research Chemico-Pharmaceut Inst im Ordzhonikidze
Zhur Obshch Khim, Vol 23, No 9, pp 1555-1559
A.number of substituted 2-aminomethyl quinuclidines
and 2-aminomethyl-3-( ?-aminoethyl)-quinuclidines
vere synthesized.

j
5,-
(L
quli., -VIA ed U.38 g.- corkspoittling f
i't T~
libiling
Unit
Were
himil.-, quinudlitifniFilliv,~k~ 2-%ithirw ikridynaftfl 3-:
Synthests W, (5-ethy1-Z-qutnuCfltlh1YlYz )car p
'Rtth v NMI V. A~ Vol I'l -the-wrt)
MI inartivelavins
p
T~F-5
in lar -.t;;; -S th, Of (Z-quinuctid
9f - Na and 2.
FTF;;-B~ IM J.
ur- 615sKnal W)i - -: 41 Jbid~ 1 To MONa fritnt 1.1-) r. g
Kni in. 23,
.-!w~To -23 X. Pfa fit 4.8 g.abs~ MOU in -added ~'EtOtf skis -[;'~Ett(? ivi
E60 was -is arlded 7.5 g." PC 0101rul t~
d
JR picolinatc-and 17 g., Et Xtienzoylhomocilicholoi -'and 8.5. v Et,. - --- ---
otr4te, (lie, M10, rcmovM bj- h6ting -bi 80% the mbxt;~-` h6ted 4 hrs;-A:SQ'- ditri'41th Cift
th --- ----------
40i0d at 880% crteled, tfutsiched in J110, v;td. with:.. Milt told
theall. layer neutmilmd wittl LUM, and 4pin -,.-F%0,t6d tre~Ltcd %vith
vvith Ft-0,yielding 55.1% red oily -EttO. jxve, 57.6%. crude
--'4-psjwr: - - iial. A-,iiti. ivifh~ 164".
I-e6bethazyclkyl 2-pyr"yt ketont:,- ~vhich irith-~-. 10-xviky!"s-pyriM. krtiirr~' which;' riol
was refluxed 4-hrs- -with. , 10 pirts - 17% pa de Rfl% -21:t4 1)
but.littsfication- I vr~s Lw~ -tG 7.
-50P MG
HCI tie roduct washed with EtA made alk. %vith -07. dAyf -Zvpyridy1-kd~str,- in oil-', viviul-
Kn: u." 4.5*- (aude),~ in. (front'i3tolivetco). Tb
d "td. with FtO,' yielding 5.$8 ff, exude
2-pyridyl kdone; - this treated- in ~ 10"~ IM'sidt. (21-g.)-iri77.5 ml, 48% Mr. trni6l (it W* wit
HtOff,with 1.05g.(MH~infiml.ibi. Et0F1andI---" 1.25 it.- lir fit 9, ml. -48% HDr. the- mist. limited 15 inill - t-Dr-
AM.- with 125 mt.' dry MejC0 yieldedza, ep
t.
Ikelatie oxalad, Yront~~, iMECtind dild. wiffi-dry Njejeo gaye
in 44.6% yield. The oily free 64m (2.89-g.) m W r
mt. 41%,HBr treated at 6V vrith 1.74p Br in 9 mi. 68%:
Hilri the mlxt.~stirrcff 20-min. at 80 , evapd. itt vacuo,
the re5idue treated with 11,2 g. KAM% In 130 ml. flio and,
60 slit.-ClICIg shnkLm 2- firs;.-the uq. -Layer-' extd. with
C1103i will the combined ClIC4 soln. vialid.
ethyl-Z-quinudUinyl 2-pyridyf kehine, W.S. DAY-o
76.2", (Et()[Q~ ifninedlately, [al V 16.7' (EtOff) after 24
-(2.47 g.) in 20.2 ml. ff IICI sbakm ~ritft~ M.
fivii. ~ The ketone ISO - snwqjx~a
Ai~solwd-arld' ~`ffvive th ;ad, m.'f tq-191 (flio-ni ti -tther),'which
nt.27c, I'dCh soln. until the orange ppi. efres. cirb
It opic d CT -,T eniot er
slight It pressure and It It U
hydrtipq~to'~t a rWrn YleMed
-175- V
.7. iy'= them , in- JP,
31iii npm o tits er'p e lieff iob-
base mrobioll'sn. -t-~Bottt
We .4na 1

-------- ----
-p
V, ', . .. . . .
i~iii tallt a
irW A
I ff
-QUIRUC 10
T nd
ed td 100,
d6ti.,
ay p P~r
londleAWded. the-juixt.
gbalea
:Pro
Colli" ind silloWw- WeNt. ivith
Iso"Th
101i theiit~Uy ticotsilixitl,
V=tp
If,
E804 sAd.-etid.JriO`CHM& Oiddll
nijk*, ~hk
-td M4. With 20 irt~ I 19
iHCI s4ft,"ma-173
4-540, (fx Ab& HtOl
-i8jo R - 701~ War -avei 10
r . Br ixt triaied
miu:r With
03 lu Br iuJ6 at SO
89A
dyl)
is
piwfii~~-Isq -90
-60 uspigaluilot I dami,'m
yieldi.4
k aHa. 2464~~. (hu;4
f!rOO!
-h
Th '(I
.~; . ~ Over.
P& id dO.44;
ITIO)
-037 1"Ill -j o4a, su; 200~
cl ve
k
15~- "K
5 T'j aswl,,th,
il6ii;bl. iiefWifaCeM44
lon ur er 0, -HCI;
f tb _tv;lpn., pvc Im 0 wbld treaftd. with
'hun Rtoll-mesco).
ra 0.92 g,
gai
'th th vnitit' li 8 the fra h
e a er rt 6. roctowl of whic
61; 5
The diaitere6tr4beric -ms~ A mj3d Air- ult.
1
if -- iethocing tri AcOH (60%),~- In: wh
they differ from the quirtine alkaloids., Both pteestalates am
vk
w

)20"
61
Rubts" ahd:B

Chein.-Pliarin; Inst., Moscow)
Zh19r,.ObAcketKJVs-m.24
,
r
2MV-02
m-4); -:d. X-74r. 3978a.-~-A iidxt-:of Etbk~
(rrorn 2A g Nx ond,40 mi ELOU)i 18M g;7phCaliQOjEt,~
and 20 g..Et a_(4~0-ijrj -1)a -I te'lidated'!I jjr$~-&t Boott
and Lreated VVitWve19
YdII!A
~:
67f
g
d
g
c
ve
,
.
Et
o%
7
lutoWdi 11w1w, OMIt hydrolyolt
iRvc acrFd dec 2314~:
Insoli ItS
-of
&j. solvents
flie I
Tit
.
.
,
MTr a Ft- 011do catalyst-in -E to H *cmtjis: cim Ra
I'lo Ins Yielding tfie, contsponding J-Cf.pi
perrdyl: aw
-
O
ieldi
h
h

ng t
ii in
t y
41721:
0i free iw
-vvhkh ftadjjy~
vicks up, I
o
J

N
j~~
, 4 9WIS
'~
dxtd'15 1
MAft cbfidd
RC
1
.
,
I jave
a
jew-scil' luimej Of thifmur "Wa i4U (l1),-dccoznp.,23Cj.;;',
'
,
and a inomq6l. Jjoftw ( i
decamp. 178* (from Etomm,
f m acid -

-
ecmp~ 210- gave.m, h
d die latt
f
er gave a
ree acid isomer
decbmp; 272 11
iii
.
, va,*,, 15 n1in, ~at
-
'
ts I
o
r
t t
:
As the Ha Thi
di-Ef ester
-
*th Br-In CHChat2Q*gmYedi~.Fj
rmf& HB

Q M W-M R 734 W, x V M :~-
;~-,~~;,
Z~ k W4 a mum NOWN-3 IF w SM M

v'`:,
4je
otilzboniisidze
--ac t fFD* fiffine PkI. V. Rishisnvf
y isle
Lraffulm ,
_Wge
"10n - ,em escarch IrL
im 'em. umir. ----
bur.. MOM Ali Z5, Krzi- W~vr
7b); C7~
sm.
Doering,- C.A. 39, .3(=s.-m-Re6tUxhsg 196 g.,'KG
nd
a
180 sid. AeOll, and 2N.5 g
r ...-A-inetltylpyridine r 10 firs., ibe mixt.,iftered, the-Mi
.-L tint theinixt*.-again
-'oncd it the b.p. rose to 17.5% and
A fluxed 10.1im. yielded 81% 2,6-dichlii,044~100rtkyf,
I lyclit%enation of this 0
mcthyl#yridine, bit ISIA ver
in aq. Meoll-tIct at room temp. gave a,mixt. of. 3
A ~4
YdrOX;Ye1hyl)4-mdAy1Pyridi:;e., (1) nuel 2,64ii:Msi
hyfr,,irthyl)-4-iffethylbridine '(11); L vittl,~ ivilfi~ st-0
rm nwitt, of the! aq-50111-witti KOII pwr 119-.73
-MI.An' ~ M5.54% the org. 6.11.
I l82-4*;,,m. 1, 73.5-5% which oncatalYtic' li'll"getirtfOll
1: yield.-; I.- Heating 3-(2-chloivethyl)-4-mctliyl'i-)-~-,',Iitic
be-
with 11:10 to 14G-50* 3 brs. in settled tu flalk AY6 1.
heattid'with AcsO gave 04.3%-acdafe 137r
Ml Ail(, in. 101-1*. This (55.6 g.), 63 9" CC13C'101
it
nit. pipetitline, and 2.2 nit. AcOlf ficated'IT firs, t 82
and the priisluct (Lin) boiled briefly with 2N 110. chill
o nit timited with - much 15% - Na2COj pve rA.2%.J
brtri;.tyt-ihyi)-4-(3,3a-itichloro-2-hydroxypro~yopyridine,,
li*.1i-8`; this heated to 70*- with'ale. K IL 2 firs. gay!
altittid. (IM which is either J,4-(J',4`-PYridi1sio)-2-me1kY
4~dropyra;%-G-carbilxylic acid (111&)~ or J,4-(4'e?!-pyridit
diWropyrim-2-actlic atid (111b), decornp; 27.14* whose
ester (from the acid and FROH.iss the presence of 11C
13G-I*, if, 1.16,15, nV 1.5230, gave an MO soft, m; 175-
In suldn. toIll thefeaction yielded a sistallaint. of Cj*11110
Wcl~
m. 172-M*, purified by way of its FJ ester. N.l 126
salt"- in.- lit-3') tlydrolysig of 'the Me ester save -
f
- --- - ---- - ----
with COjA there. fit obtairfed.7-1
bot idine -in 2rP-2
Car YPs"34)i7r
'_ndds and b:i-.c%,-hcating this w
E.: 85.8% Et mticr (IV), ni., lor)-~10 I
l74-W),, inve-
AV-4ith Ac,O
carhe1ha3q6"APvridine, b#.* 14!
l- in. 140.&-1_5'~. (linistri Mcsco)..:
Ptoi in ~ Etol t - I . ~
_1 among OC
A34)4wt2
-car I Pzydhy1)PiPeHo
gave slik- with _. picric. pocrolonk

ICI t
IM'"ll t"itral" lath r"VeL71.270

1 b c1ho.i~cihY)-N-act-tylitipirldind~--. i
*
_'
*
_l i%1p
IIl7
.IATl3. Hydroitintlith
1
5
-
-0 0

ml IM-11
, t6 MrAli Fil? 1.4718, v
.

(2
mans. ~VlfhA~.OftgaviVl.: VI
'
Molt
its file presence of it It
ttle
in
EtOAc while the residue; after dry
a,.
di- mist of prodticts.wilkh was talks
from the r6idue; yielding 79%, IN
. -
1

FJ

f
M
- 1-.1170, #V 1.4982_:Tre
Is

. in CIICI. 41 ill T
iii-ence of powd.
,
h.j
T'
deriv of VIT. eq.i 207~10% its, 1

N fl
re lixed 5 lirs.. irith dry M011-11C
.

N-Bs &Fig. of V. bis-3 MI-6 ,
I
fi~v
74
MIT -over Pt. gave -~J-,
ei(din~e
't j Na), .W-
ta_-
tied 5 Is
rs. With 90.6%
F HCt gave on. distn.-
in:vasnsid at 80' gave a. -
and -co -441
dW."Ioi
P bej
With R.4Cl
tent of V11
've ~37~
0'- tell
P 1 5190, its
ve
P i
-6-
77

F".
TPWKMI-~Pl:
forr-d by hydrolysis of
t. hl,,,,-2-bvdr~uxvpropyl)pyridine (ci. premding abtr.).
Ir~ FtOH ovri Fff~ v rr~m
d-'~4h.xY"SnuJ.dtne. b- 110-70 aV 1 4". d-M 1 133
ruixt of 2 stereotsurners; all sat" were ods- l"efluxing Id
r-un,-t with K,4-1 t, 4-~,
hrs~ with concd - HCI gave 99.2%
dixe-~,-arbax7icc acid-HC7. amarphom powder; --catment
with NaOH and evap.. gage the free acid, the ame being
obtaited by treatment of the RCI salt with AgsO ' followed.
Ila IM 2(K)' The mixt. hv dectimpa. of the Ag salt with HTS. The free acid is a
"i I --d thc otl ery ~iygrowoptc powder. Treatment with ale. HCI at.

;/~"ie~~idWiOr~d-u'ctiiithisyatheWs*~f itlciilor actilildifie
itiv,
TS.
r

1
-061 -13M-A I
hur
hChel Kbilp
25
z
.
.
i 9-
Y,
&4iydrox
and 4N) Jill; 1100, lit a Wilib 5 hirs-at 66~mr Will fullf)VAN
I
by. ~e J,; was,
purified by solit, its - hot cort6di. 1 [Cf. icmtiti 9; septi. bf th L - -

ptd. HCI salt.
p of
the pptd. tuottub ydra te and va~-utim'ttry ihj,; yielding"t

..'drale, in. kite toostitutioll'.:, "-,
-d by Stevritsi-el al.;XA'~
and 20 oil- POCh-heaW in seal6d amput 5 lmi~'at M-0 0
id tlt~u: qtJOnchc4 in Ice-, 1~mve` tfw enitle: jir6duci;..h1rh-
at
Rl Slit
a -hotAigirmite-anddis

'
169:

ni.69-70% identical with 1116 fituduaprep ftccording-p*ii:1
d
,
'
;
(tee. dlj.-*~J dods~
its-Cf with
uot law,
-

-rdok of 2MG-W..
heating with Lc4critt - cl&vei, L
KOA
heated With RtOll''grves L"Thit Itigh'temp;:'reaction of--
'
POC13 with I probatilk goes lit stages, under , 100'. the fumq
mied ~i~IdWi.ii-'dichlpmph,6iphate%deriv.-at *the
ring 5 op
'
(ion with POCh Ot 180* y1elds Iff.- A46 In 1.~ Xi
am
al
V.S.S.R. 25, 1,304-7( (H110, Ounslaffo
R

;ic jz

~m kg7N- ;~ %,f-, bus N ~

0
RUBTSOV, M.V.; YAKHONTOV, L.N.
Synthesis of the ethyl aster of 5-(~ -metho37ethjvl)quiuaclidiue-,
carboxylic acid-2. Zhur.ob.khim. 25 no.9:1743-1747 S 155(MIRA 9:2)
l.Vsaioyuznyy nauchno-issladovateliskiy khimiko-farmatsevtichaskiy
institut imeni S.Ordzhonikidze.
(QuinuclidinecarboVlic acid)

777
e %
vsyttthesla -at, 1H meth
[Zmethoxe6thjik- '
=rrld e~- 16D-1
N. Yak ntov-($.- &Wzc 20,mlePO"'Im"Sts tnbetlhis'.-it,
1d
M
u

. " Set. Research . IUU4,
Adodc6w).
P
h
X

qZkw.~0bskchef Khimi
N irN kfft
11344'!
grit
all
---
_
lu-M-- .2Adkhtor6-34Z-ihioicoithyl)4-methyloyridint- (1).~ with- 2
'
2(g)
l
Olt S
ith
KOH I
1
H
d iddifiiittoi ~
,
rd. Na In Uto was addcd-402 It and the mbLL
-
'
7~=
4 10
m
d
l
. 4
n
su
t
ry
tirs. an
t w
g.
142-3'
l
whi
h do
ot
b
l
s
HCl
8
8
3
(11) uxc
Is
rtf
ftcuted
withl(l W. Mel, an
d 00 lta..
-
':
1
0
b
h
Wo
W
ft
-v
-
ana
c
e
n
gave
.
S.
sy
vg
, 4
f
,
'form 11c1 "It
icrate of lutthlok and which
ields by -
-
nj-
s Inixt., ho 154
.
T
e In
a
-yieWini
i
:-
W,
-7A j
ntl the resid
hilk-d
M
ldin
i
"
. p
y
.,
';R&AuxInj 4
~reductlou over Pd A-colUdIne
1, fresis
2 -
e
. Wjs c
l~
I
, y
, a
g
22
ieldin
5
1 With BxC1 In Cjl
B
,
.
~
A
0 with 6
I and 50 ml
yridine 6 ha
gave 2
7
0
dry .
Was Fe
UXL4
#, y
g
of Ill was
the Bt dtdv
(VI) of UI and IV
V
luk
.
.
,
.
,
C.
c&
p
11, big 130-40*i and 2.3 C. recovered 1. 6 18"0.
' I
C
"
,.
;
left in the dista. resklue. -~Thq mixed dIsMte Was then
IA*
'4 readily pve
(I A g.) treated with 2.4 g. Brie In CHC
177-8*
- Refluxin
C
which does not form salts
dibromi& treated with dry HCl in Rts0 v

h
li
h &ld
-Inc 2.74 c; 1V.AYC1 while
~:; -J"
d
till IMU
.
hi
,
s
,
M.9 g. 3-(2-acetosyethyl) analog of I to 1.51.20/0 ate. HC1
ill
3 h
98
2
h
d
l
f 1
b
) e mot
er
t
qum
I Ms. I When Uri-AmOH (i9 m ,
o
t.) was rotted wkh 10.1 t
-
r3. gave
rosye
ana
) o
og (
o..,
,
y
t
f.%
1864'
73-5
U
d
V,
h
fl
d h
ith B
C1 I
C
H Ns in Meft and the cooled mizL treated with 70 jr. u and

i
d 12
r
x
. m.
re
uxe
rs. w
. w
z
n
s
a
oil% 6:;;ZryJ anWog,-b&234-5*, m. 110'. A
re'
and 60 ud
H
8
kw H
3
K
MePh was rre
stirred 9 hrs., then treated with 35 ad. Mel and s
hys.- longer; them was obtained 9.1 9- M,-b& IM-Vt and
h d
W
i
d
i
h
.
.
g.
g.
;
,
fluxed I hr. and treated with 19.3 E.- 1U in MePb:. after I -
'
bra
at room temp
and treatment with 4
5 =L Mel
the mixt w
4
was treate
t
, wh
c
rY
a mixed fraction, be 130
-iding 45.9% IVACJ, *hue the residual,
liel in Etio, YP
-
6*
-A
eactio
n
i
&
1
i
i
28
VL b
1&3
.
.
.
.
.
was 12 bra. Yielding 90.7% 6-ckkrP4-mdky1-S~?-; .
-
-
s
m
r r
n ru
.:
,-_.
t
u
iqu
, gave
70
-

WX-dikydrqfiirsoo)~~iue (TY),- bu 187-00. m- 45."0; ve7l,O%Vltinditiov~ykwotlv."Hr
t
`T
llcl
91
W
7
3%
HCW saft, in. W,8.5
k hy-1,
- - -- - - - .
drocenatian of V1 over P4
1
%
re
I --L-1~~J- ' I-- I

77~~
r

2-

Y
J,
!
Yn
1A TIPM Fffi:qW-R
ZAW. : ObskcAel
-2
dW%
WCli 14 hm; at WV
!:;`."followed by rembvW bfezceis~socli MaWand-ad&-ol
e uc
PiOd ttOSA -PhbMM'ihi13hO4t-2vj(oUowedb
th
Stirring -2 hn

fig
ide of 4
Th Is ~ i TV
d ~ with 0
21
TT) ue
l
.
a
t
g
~W a treatment' and Shuldng auv`;;,~~ -
~:Vi. followed
-'
with NUISO
Wlnv
th
~bls
LRE
d&
d I
O
?
t
o
a
u
a
aa
se W -
. uc
a
~ . P
6Po.IIWjth;Satd.r:W8,CO, gaVt,
'cleou 6

d- I-im.: HCI "ft.
decon p
ine, hi~.
.,,rate decomp.,218-19*;~pk
147
e, gives .2;-,---~,.
-and a;-Ag miffor~
T r with' fui:lisl~'~~ Jorms
-M Kowhnioff
G
.

J:`
now

Vnew paths of svntheds at 2 in
tuLludid* ".1,
it-
~h if, 1 4A"
-Py, C~.P-11-

rehTi4S a, 5'/Pj'rOr-siS , , , .
. , I. ~ - I '4f, 7' :. 0-, A, 11, .1. ,, i- , 1 -.1, 7 ~ . .- . 1. -1
. '! ill. ~111 11 ~ I '. ll, ! I,.::. .,?I,
.1 . .. --'~wfl !, ! ~ - I .*1 A . f-41-1-11 Ill
)" . ;.. " , '. 1,! t , , ,, ! I.., : 1.' 17' h,, j, ,.
.1 11 1 - . . .

- 1 -~ '.fs.

S.01bamis of
.'fF
G M iiK~
2.9 .7li~".~fuuiu'mlgyl'q~uinuAc4dint. 3 tul dry pyr~dinr.
mW&B drops -.piperidine witiz G;Ek . CH -),4
a%ye afteiex I _ lh;.
m.;w4th 9t,Oj 66%iil
.eminalonate, CulluOtN, bq 14:3-36 u'Do IA821. Refluxed
with coned. HCI 13 Urs. It gave 90% A42-quinadidicyll3crylic
acsd-HCI, in. 197-8'. which hydrogenated over Raney IFI
941le #-(2-qujnurAdinyl)ProPwnic acid-11C. decamp. 215-
113', al:wj Ginned from upon hydrulyai!i of the cater, h.
14 )-W. , obtained-by camlenvtIbm of Z:bmunt-A-ah a
XL _~p-
nuclidine-IffIr the-
acid IIICI sdt with SOCIt. folitivred by- redIuxing-the crud r
acyl chblTide with Mott g;%ve a 0-(2-quij%udWmvi)prvph,-
n.le. t-hocd ~~ the m4h,adale, m. 87 U*, in 37 5% yuld

-1'-RtMT
USSR/Organic Chemistry Synthetic Organic Chemistry, E-2
Abst Journal: Referat Zhur - Khimiya, No 1-9, 1956, 61543
Author: Rubtsov,- M. V.J. Nikitskaya, Ye. S., Usovskaya, V. S.
Institution: None
Title: Alkamino Esters of Some Heterocyclic Acids as Possible Hypotensive
Remedies
Original
Periodical: Zh. obshch. kbimii,, 1956, 26, No 1, 130-134
Abstract: There have been synthesized the diethylaminoethyl eaters of dipico-
linic (I), dipipecolinic (II), N-methyl dipipecolinic (111), 6-
methyl-~picolinic; (IV), 6-methylpipecolinic (V), 1,6-cimethyl
pipecolinic (VI), and quinuclidine carb*lic-2 acid (VII). On
pharmacological investigation it was found that the di-methyl
iodides of VI and VIT have high ganglion-blockinj activity. A
mixture of -inic acid (VIII) and 30 ml SOC1 is boiled,
ipico
until compl ely,dissolived hours) heat the thus iormed di-acid
chloride (IK) with 30 ml diethyla-minoethanol (X) for 6 hours at
Card 1A

'USSR/Organic Chemistry - Synthetic Organic Chemistry, E-2
Abst Journal: Referat Zhur - Khi iya, No ig, 1956, 61543-
Abstractt 110-1150; 1 is obtained with a yield 55-4%., BP 214-2150/0-5 mm;
dihydrochloride.MP 190-1910j-dimethyl iodide MP 200-2020. Analo-
gously frcm 6-methyl picolinic acid (XI) is obtained.IV (yield
77%, BP 128-1310/0.25 mm; hydrochloride, MP 147-1490; methyliodide,
MP 115-1170) and 4M quinuildine carboxyl4c-2 acid, there is ob-
tained VII; yield 73%, BP 16o-1640/9 mm, difethyl iodide MP 222-2230
(from acetone). 10.7 g of I are,hydrogenated in 165 ml of2-5%,
solution of HC1 in alcohol (o.63 9 Pt02 -200., 40-60 cm of.water
column, 9-10 hours); water is ad&d, the mixture is filtered..
evaporated to dryness, treated with 50% solution of KpCO and ex
tracted with ether; II is obtained with a yield 86%, BP 18'2-184~70.2
mm; trihydrochloride MP 232-2330. Analogously is prepared V.,.yield
52-3%, BP 98-1000/0.2 mm; dihydrochloride MP 2200. By boiling of
DC with absolute alcohol is synthesized the diethyl ester of I
(XII), yield 84-7%, BP 127-1280/o.2 mm mp 44-460. Analogous .1y is
prepared the ethyl ester of XI (XIII), yield 87.3%, BP 79-810/0.25
mm,* hydrochloride MP 74-750. By hydrogenation of:XTI and XIII over
Pt (from PtOp) under the above-described conditions are obtained
respectively the cliethyl ester of dipipecolinic acid (XIV), yield,
Card 2/3

---- --- ----
'USSR/Organic Chemistry Synthetic Organic Chemistry, E-2
Abst Journal: Referat Z4r - KhimiYa, No 19, 1956, 61543
Abstract: 90~j BP 103-1050/0.25 mm, and the ethyl eater of 6-methyl
pipecolinic acid (XV), yield 92~, BP 99-1000/13 mm; hydrochloride
W 213-2150- Mixture of 4.27 g XIV 1 32 g CH3J-and 23 ml abso-
lute alcohol heated for 6 hours at 40:4t5o~ evaporated in vacuum,
residue extracted with dry C6R6, the insoluble hydroiodife Of X1V
is filtered off and from the benzen e extimct is recovered the di.-
et ester of N-methyl dipipecolinic acid (XVI), yield'52-7%. BP
hyl
10n)7 0/0,2 mm. Analogously is prepared the ethyl ester of 1.,6-~
_V8
'Eby
dime 1 pipecolinic a. cid,,yield 43-7%, BP 53~540/0.2 mm.; hydro-
chloride NP 198-2000. In 7 ml of.X are dissolved 0.01 g Na, added
with stirring 1.32 g XVI, heated 3 hours at 1500 (distilling off
the alcohol) excess of X is distilled off, the Iresidue is,treated
with 50% solution K2C03 and extracted with et$W; ITI is thus ob-
tained, yield 51.2%, BP 176-1780/0.2 mm; methyl iodide and hydro-
chloeLde are oily subsVII01 Analogously is synthesized VI
yield 44.7%, BP lo6_108-07-0-25 mm; dimethyl. iodide MP 201-2026.
Card 3/3

USSR/Organic Chemistry Synthetic Organic Chemistry, E-2
Abst journal: Referat Zhur Xhimiya, No 19, 1956, 61542
Author: Mikhlj-na, Ye. Ye.
Institution: None
Title: Preparation and Properties of Ethyl-N-(quinuclidyl-2)-urethane
Original
Periodical: Zh. obshch. khl 11, 1956, 26, No 1, 135-138
Abstract: Described is an attempt to synthesize 2-aminoquinuclidine from
quinuclidine carboxylic acid-2.(I) over its hydrozide (II) accord-
ing to curtius. On interactio&11111- n with is0-C5H1 1-ONO (III) in
alcoholic solution of HC1 therL7 is obtained ethyl-(IV) and in the
solution of HCl in iso-c5HllOH respectively the isoamyl (V)-N-
(4uinuclidyl-2)-urethane; together with IV as a by-product were
isolated ethyl-(VI) and~with V the isoamyl (VII) ester of I. On
saponification of.IV.by action of dilute HC1 was obtained NJkC1
and amorphous polymer.of dehydroquinuclidine (VIII). On heating
of IV with C6H5CH2NH2 (1K) to 10CP evidently takes place
.Card 1/3