SU608473A3 - Method of preparing cyan-derivatives of pyridines or salts thereof - Google Patents

Method of preparing cyan-derivatives of pyridines or salts thereof

Info

Publication number
SU608473A3
SU608473A3 SU752198509A SU2198509A SU608473A3 SU 608473 A3 SU608473 A3 SU 608473A3 SU 752198509 A SU752198509 A SU 752198509A SU 2198509 A SU2198509 A SU 2198509A SU 608473 A3 SU608473 A3 SU 608473A3
Authority
SU
USSR - Soviet Union
Prior art keywords
ether
solution
ethyl acetate
oil
salt
Prior art date
Application number
SU752198509A
Other languages
Russian (ru)
Inventor
Джеймс Балдвин Джон
Original Assignee
Мерк Энд Ко., Инк (Фирма)
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US05/533,385 external-priority patent/US4000282A/en
Application filed by Мерк Энд Ко., Инк (Фирма) filed Critical Мерк Энд Ко., Инк (Фирма)
Application granted granted Critical
Publication of SU608473A3 publication Critical patent/SU608473A3/en

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Landscapes

  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Claims (1)

25 мл дизтилового эфира кажддай раз). Экстрагированный водный слой делают основным путем добавлени  насыщенног водного раствора карбоната натри . Этот водный раствор затем экстрагируют этилацетатом (3x25 мл) и раство этилацетата сушат над сульфатом натри . Высушенный этилацетатный раствор затем концентрируют при пониженном давлении (20 мм рт.ст.) над паро с Получением масла. Масло хроматогра фируют на алюминии. Хроматографическ фракции концентрируют с получением масла, которое раствор ют в диэтиловом эфире. К этому раствору эфира до бавл ют этанольную НС6 (насыщенный раствор до тех пор, пока не будет пол ностью закончено отделение твердых веществ. Отделенные полутвердые продукты перекристаллизовывают из изопропанола /эфира (эфир добавл ют к изопропанолу до помутнени ) с получением 1 г (S) -2-(3-шрет-бутиламино-2-оксипропокси )-3-цианпиридин-гидрохлорида ,, т. пл. 161-163°С. В примере получают S -изомер пиридина , рацемат синтезируют путем использовани  рацемического ( S/В)-оксазолидина , В-изомер получают, исполь зу  R-оксазолидин. Свободный амин получают из соли, полученной по указанному примеру, любым известным способом, например путем обработки соли основанием (например , едким натром) в растворе и экстрагировани  из него свободного амина Использу  данную методику получают )-2-(З-изопропиламиио-2-оксипропокси) 3-цианпиридин-гидрохлорид с примением соответствующего N -изопропилсазолидина вместо N -tnpem-бутилоксалидина . Формула изобретени  Способ получени  цианпроизводных ридинов общей формулы , -СЫ ,мС ,Н2 где К - изопропил или мгрерг-бутил или их солей, отличающий  тем, что соединение общей форлы О СНг--р-J где В имеет указанное значение; К означает водород или альдегидный таток, подвергают гидролизу насыщенным створом нее и целевой Продукт выдеют в свободном виде или в виде соли. Источники информации, прин тые во имание при экспертизе: 1. Вейганд-Хильгетаг, Методы эксримента в органической химии, М., Хими  , 1968, с.362.25 ml of diztile ether every time). The extracted aqueous layer is made basic by the addition of a saturated aqueous solution of sodium carbonate. This aqueous solution is then extracted with ethyl acetate (3x25 ml) and the ethyl acetate solution is dried over sodium sulfate. The dried ethyl acetate solution is then concentrated under reduced pressure (20 mm Hg) over steam to give an oil. The oil is chromatographed on aluminum. The chromatographic fraction was concentrated to give an oil, which was dissolved in diethyl ether. Ethanol HC6 was added to this ether solution (saturated solution until the solids were completely separated. The separated semi-solid products were recrystallized from isopropanol / ether (ether was added to isopropanol until cloudy) to obtain 1 g (S) -2- (3-shret-butylamino-2-hydroxypropoxy) -3-cyanopyridine hydrochloride, mp 161-163 ° C. In the example, the S-pyridine is obtained, the racemate is synthesized using racemic (S / B) -oxazolidine, the B-isomer is obtained using R-oxazolidine. Free amine is obtained from the salt obtained in the indicated example by any known method, for example, by treating the salt with a base (e.g., sodium hydroxide) in solution and extracting the free amine from it using this procedure to obtain) -2- (3-isopropylamio-2-oxypropoxy) 3- cyanopyridine hydrochloride using the corresponding N-isopropylsazolidine instead of N-tnpem-butyloxalidine. The invention The method of producing cyano derivatives of Ridines of the general formula, -СЫ, мС, Н2 where K is isopropyl or mg-reag-butyl or their salts, characterized in that the compound of the general formula O СНг is p-J where B has the indicated value; K means hydrogen or aldehyde tatok, is subjected to hydrolysis with a saturated target and the target product is isolated in free form or in the form of a salt. Sources of information accepted for examination during the examination: 1. Weigand-Hilgetag, Methods of experiment in organic chemistry, M., Himi, 1968, p. 362.
SU752198509A 1974-12-16 1975-12-15 Method of preparing cyan-derivatives of pyridines or salts thereof SU608473A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/533,385 US4000282A (en) 1974-12-16 1974-12-16 2-(3-tert. butyl or isopropylamino-2-hydroxypropoxy)-3-cyanopyridines

Publications (1)

Publication Number Publication Date
SU608473A3 true SU608473A3 (en) 1978-05-25

Family

ID=24125731

Family Applications (2)

Application Number Title Priority Date Filing Date
SU752198509A SU608473A3 (en) 1974-12-16 1975-12-15 Method of preparing cyan-derivatives of pyridines or salts thereof
SU762404901A SU618040A3 (en) 1974-12-16 1976-09-28 Method of obtaining cyanpyridine derivatives or salts thereof

Family Applications After (1)

Application Number Title Priority Date Filing Date
SU762404901A SU618040A3 (en) 1974-12-16 1976-09-28 Method of obtaining cyanpyridine derivatives or salts thereof

Country Status (16)

Country Link
AT (1) ATA946575A (en)
CS (1) CS188983B2 (en)
DD (1) DD122527A5 (en)
DK (1) DK544875A (en)
EG (1) EG11860A (en)
ES (3) ES443459A1 (en)
FI (1) FI753382A (en)
HU (1) HU171489B (en)
IE (1) IE42373B1 (en)
IL (1) IL48611A0 (en)
NO (1) NO754088L (en)
NZ (1) NZ179476A (en)
PH (1) PH12275A (en)
RO (1) RO68167A (en)
SU (2) SU608473A3 (en)
ZA (1) ZA757804B (en)

Also Published As

Publication number Publication date
ZA757804B (en) 1977-07-27
SU618040A3 (en) 1978-07-30
CS188983B2 (en) 1979-03-30
ES443459A1 (en) 1977-08-01
NZ179476A (en) 1978-03-06
ES458429A1 (en) 1978-11-16
EG11860A (en) 1977-11-30
DD122527A5 (en) 1976-10-12
ATA946575A (en) 1979-09-15
DK544875A (en) 1976-06-17
HU171489B (en) 1978-01-28
FI753382A (en) 1976-06-17
PH12275A (en) 1978-12-12
IE42373L (en) 1976-06-16
IL48611A0 (en) 1976-02-29
ES458425A1 (en) 1978-03-16
IE42373B1 (en) 1980-07-30
NO754088L (en) 1976-06-17
RO68167A (en) 1981-11-24

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