CH125406A - 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
- CH125406A CH125406A CH125406DA CH125406A CH 125406 A CH125406 A CH 125406A CH 125406D A CH125406D A CH 125406DA CH 125406 A CH125406 A CH 125406A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid derivative
- preparation
- carboxylic acid
- quinolinecarboric
- 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)
Description
Verfahren zur Darstellung eines substituierten Chinolincarbonsäurederivates. Es wurde gefunden, dass man zu einem substituierten Chinolincarbonsäurederivat ge langt, wenn rnan auf a-Halogen-r-chirrolirr- carbonsäurehalogenid Diäthylamin einwirken lä13t und das erhaltene a-Halogen-i--chinolin- car-borrsäur-ediätlrylamid mit alkalischen Propy- lierungsrnitteln,
wie zurr Beispiel Alkali-n- propylat oder n-propy lalkoholischen Alkalien, umsetzt.
Das auf diese Weise gewonnene a-n-Pro- pyloxy-r-clrinolinearbonsäure-diäthylamid bil det farblose Kristalle vom Schmelzpunkt<B>611).</B> Es ist in Mineralsäuren und in den meisten orga nischen Lösungsmitteln ausserm kaltem Petrol- äther leicht löslich.
Die neue Verbindung soll therapeutische Verwendung finden.
<I>Beispiel:</I> Eine benzolische Lösung von 2,2 Teilen a- Chlor#-r-chirrolincarbonsäurechlorid wird unter Kühlung allmählich mit<B>1,5</B> Teilen Diäthyl- amin versetzt. Nach beendeter Reaktion wird vom abgeschiedenen Diäthylaminchlorhydrat abfiltriert, mit Benzol nachgewaschen und das Lösungsmittel abdestilliert. Aus Alkohol umkristallisiert bildet das a-Chlor-r-chinolin- car-bonsäure-diäthylamid farblose Kristalle vom Schmelzpunkt 124'.
10 Teile a-Chlor-r-chirrolirrcarborrsäure- diäthylamid werden mit einer Lösung von 1 Teil Natrium in n-Propylalkolrol am Rück- Russ gekocht. Nach beendeter Reaktion wird der n-Propylalkohol abdestilliert und der Rück stand mit Äther und Wasser ausgeschüttelt. Die ätherische Lösung hinterlässt beim Ver dampfen ein fast farbloses Ö1, das allmählich erstarrt.
Das a-rr-Pr,opyloxy-r-chinolirrcarborr- säure-diäthylamid lässt sich aus Petroläther umkristallisieren.
Statt mit Natrium-n-propylat kann die Umsetzung auch mit andern alkalischen Pro- pylierungsmitteln, wie zum Beispiel mit Als kali in wässerig n-1>ropylalkoholischer Lösung erfolgen.
Process for the preparation of a substituted quinoline carboxylic acid derivative. It has been found that a substituted quinolinecarboxylic acid derivative is obtained if diethylamine is allowed to act on the a-halo-r-chirrolircarboxylic acid halide and the a-halo-i-quinolinecarboric acid diethylamide obtained with alkaline propyling agents ,
such as alkali n-propylate or n-propy lalcoholic alkalis, for example.
The an-propyloxy-r-clrinolinearboxylic acid diethylamide obtained in this way forms colorless crystals with a melting point <B> 611). </B> It is easily soluble in mineral acids and in most organic solvents apart from cold petroleum ether .
The new compound should find therapeutic use.
<I> Example: </I> A benzene solution of 2.2 parts of a-chloro-r-chirroline carboxylic acid chloride is gradually admixed with 1.5 parts of diethylamine while cooling. When the reaction has ended, the precipitated diethylamine chlorohydrate is filtered off, washed with benzene and the solvent is distilled off. Recrystallized from alcohol, the a-chloro-r-quinoline-carboxylic acid diethylamide forms colorless crystals with a melting point of 124 '.
10 parts of a-chloro-r-chirrolirrcarborric acid diethylamide are boiled on the back carbon black with a solution of 1 part of sodium in n-propyl alcohol. After the reaction has ended, the n-propyl alcohol is distilled off and the residue is extracted with ether and water. When evaporating, the ethereal solution leaves an almost colorless oil, which gradually solidifies.
The a-rr-Pr, opyloxy-r-quinolirrcarborric acid diethylamide can be recrystallized from petroleum ether.
Instead of using sodium n-propoxide, the reaction can also be carried out with other alkaline propylating agents, such as, for example, with Al-potassium in an aqueous n-propyl alcoholic solution.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH125406T | 1926-04-30 | ||
CH124228T | 1929-04-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH125406A true CH125406A (en) | 1928-04-16 |
Family
ID=25710213
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH125406D CH125406A (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) | CH125406A (en) |
-
1926
- 1926-04-30 CH CH125406D patent/CH125406A/en unknown
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