CH125399A - Process for the preparation of a substituted quinoline carboxylic acid derivative. - Google Patents
Process for the preparation of a substituted quinoline carboxylic acid derivative.Info
- Publication number
- CH125399A CH125399A CH125399DA CH125399A CH 125399 A CH125399 A CH 125399A CH 125399D A CH125399D A CH 125399DA CH 125399 A CH125399 A CH 125399A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- preparation
- acid derivative
- quinoline
- quinoline carboxylic
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
Description
erfahren zur Darstellung eines substituierten Chinollincarbonsäurederivates. Es wurde gefunden, dass man zu einem substituierten Chinolincarbonsäurederivat ge langt, wenn man auf a-Halogen-r-chinolin- carbonsäure-halogenid Diäthylamin einwirken lässt und das erhaltene a-Halogen-9--chiriolin- carbonsäure-diäthylamid mit alkalischen Äthy- lierungsmitteln, wie zum Beispiel Alkaliäthylat oder äthylalkoliolischen Alkalien, umsetzt.
Das auf diese Weise gewonnene cc Äthoxy- r-chinolincarbonsäure-diäthylamid bildet farb lose Kristalle vom Schmelzpunkt 68 . Es ist in Mineralsäuren und in den meisten or ganischen Lösungsmitteln ausser in kaltem Petroläther leicht löslich.
Die neue Verbindung soll therapeutische Verwendung finden.
<I>Beispiel:</I> Eine benzolische Lösung von 2,2 Teilen (x-Chlor-7--chinolincarbonsäurechlorid wirdunter Kühlung allmählich mit 1,5 Teilen Diäthyl- amin versetzt. Nach beendeter Reaktion wird vom abgeschiedenen Diäthylaminchlorhydrat abfiltriert, mit Benzol nachgewaschen und das Lösungsmittel abdestilliert. Aus Alkoho: umkristallisiert bildet das a-Chlor-r-chiriolin carbonsäure-diäthylamid farblose Kristall( vom Schmelzpunkt 1241'.
10,5 Teile a-Chlor-r-chinolincarbonsäui#e diäthylamid werden mit einer Lösung 1 Tei Natrium in Äthylalkohol am Rückfluss ge kocht. Nach beendeter Reaktion wird de: Alkohol abdestilliert und der Rückstand mi Äther und Wasser ausgeschüttelt.
Die äthe rische Lösung hinterlässt beim Verdampfei ein fast farbloses Öl, das allmählich erstarrt Das a-Äthogy-r-chinolincarbonsäure-diäthyl amid lässt sich aus Petroläther umkristalli sieren.
Statt mit Natriümäthylat kann die Um Setzung auch mit andern alkalischen Äthy lierungsmitteln, wie zum Beispiel mit Alkal in wässerig alkoholischer Lösung erfolgen
experience for the preparation of a substituted quinolline carboxylic acid derivative. It has been found that a substituted quinoline carboxylic acid derivative is obtained if diethylamine is allowed to act on a-halo-r-quinoline-carboxylic acid halide and the a-halo-9-chirioline-carboxylic acid diethylamide obtained is treated with alkaline ethylening agents , such as alkali ethylate or ethyl alcoholic alkalis.
The cc ethoxy-r-quinolinecarboxylic acid diethylamide obtained in this way forms colorless crystals with a melting point of 68. It is easily soluble in mineral acids and in most organic solvents except in cold petroleum ether.
The new compound should find therapeutic use.
<I> Example: </I> A benzene solution of 2.2 parts of (x-chloro-7-quinoline carboxylic acid chloride is gradually added with 1.5 parts of diethylamine while cooling. After the reaction has ended, the separated diethylamine chlorohydrate is filtered off with benzene The a-chloro-r-chiriolin carboxylic acid diethylamide, when recrystallized from alcohol, forms colorless crystals (melting point 1241 '.
10.5 parts of a-chloro-r-quinolincarbonsäui # e diethylamide are refluxed with a solution of 1 part of sodium in ethyl alcohol. After the reaction has ended, the alcohol is distilled off and the residue is extracted by shaking with ether and water.
The ethereal solution leaves behind an almost colorless oil on evaporation, which gradually solidifies. The a-ethogy-r-quinolinecarboxylic acid diethyl amide can be recrystallized from petroleum ether.
Instead of using sodium ethylate, the reaction can also be carried out with other alkaline ethy ling agents, such as, for example, with alkali in an aqueous alcoholic solution
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH125399T | 1926-04-30 | ||
CH124228T | 1929-04-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH125399A true CH125399A (en) | 1928-04-16 |
Family
ID=25710206
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH125399D CH125399A (en) | 1926-04-30 | 1926-04-30 | Process for the preparation of a substituted quinoline carboxylic acid derivative. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH125399A (en) |
-
1926
- 1926-04-30 CH CH125399D patent/CH125399A/en unknown
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