CH157849A - Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. - Google Patents
Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid.Info
- Publication number
- CH157849A CH157849A CH157849DA CH157849A CH 157849 A CH157849 A CH 157849A CH 157849D A CH157849D A CH 157849DA CH 157849 A CH157849 A CH 157849A
- Authority
- CH
- Switzerland
- Prior art keywords
- diethyl
- acid
- preparation
- quinolinecarboxylic acid
- propylenediamide
- 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)
Description
Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolinearbonsäure. Es wurde gefunden, dass man zu einem basischen Derivat einer substituierten Chino- lincarbonsäure gelangt, wenn man auf Säure halogenide der 2-Halogen-4-chinolincarbon- säure asymmetrisches Diäthyl-1,3-propylen- diamin einwirken lässt und das erhaltene 2 - Halogen-4-chinolincarbonsäure- diäthyl-1,3- propylendiamid mit alkalischen Mitteln,
die zur Einführung der Butyloxygruppe dienen, umsetzt.
Das 2-n-Butyloxy-4-chinolincarbonsäure- diäthyl-1,3-propylendiamid bildet farblose Kristalle vom Schmelzpunkt<B>630.</B> Die Base ist in kaltem Petroläther schwer löslich; in warmem Petroläther, wie in den übrigen organischen Lösungsmitteln ist sie leicht lös lich. lUit Säuren gibt sie neutrale, in Wasser leicht lösliche Salze.
Die neue Verbindung soll zu therapeuti schen Zwecken Verwendung finden. <I>Beispiel:</I> Zu einer Lösung von 1,3 Teilen asymme trischem Diäthyl-1,8-propylendiamin in 45 Tei- len 10 /oiger Natronlauge gibt man unter Kühlung und ständigem Umrühren allmäh lich eine benzolische Lösung von 2,2 Teilen 2-Chlor-4-ebinolincarbonsäurecblorid zu.
Nach beendigter Reaktion wird die benzolische Lösung abgetrennt, die gebildete Base mit Salzsäure ausgezogen und mit Soda wieder ausgefällt. Man nimmt die Base in Äther auf, vertreibt das Lösungsmittel und kristalli siert sie aus Petroläther um. Das 2-Chlor-4- chinolincarbonsäure - diäthyl -1,3 - propylendi- amid bildet farblose, blättrige Kristalle vom Schmelzpunkt 72 0. In den meisten organischen Lösungsmitteln ist die Base leicht löslich; mit Säuren bildet sie neutrale, wasserlösliche Salze.
16,7 Teile 2-Chlor-4-chinolincarbonsäure- diäthyl-1,3-propylendiamid werden mit einer Lösung von 1,3 Teilen Natrium in Butyl- alkohol gekocht. Hierauf wird der Butylal- kohol abdestilliert, der Rückstand in Äther aufgenommen und mit Wasser gewaschen. Nach Entfernung des Lösungsmittels verbleibt das 2-n-Butyloxy-4-chinolincarborrsäure-di- äthyl-1,3-propylendiamid als Öl, das alsbald zu farblosen Kristallen erstarrt. Die Base lässt sich aus Petroläther umkristallisieren.
An Stelle einer Lösung von Alkalimetall in Butylalkohol können auch andere Mittel, die zur Einführung der Butyloxygruppe die nen, Verwendung finden, zum Beispiel Alkali hydroxyd in Butylalkohol.
Process for the preparation of a basic derivative of a substituted quinolinearboxylic acid. It has been found that a basic derivative of a substituted quinolinecarboxylic acid is obtained if asymmetric diethyl-1,3-propylenediamine is allowed to act on acid halides of 2-halo-4-quinolinecarboxylic acid and the 2-halogen obtained is allowed to act -4-quinolinecarboxylic acid diethyl-1,3-propylenediamide with alkaline agents,
which serve to introduce the butyloxy group, converts.
The 2-n-butyloxy-4-quinolinecarboxylic acid diethyl-1,3-propylenediamide forms colorless crystals with a melting point of <B> 630. </B> The base is sparingly soluble in cold petroleum ether; in warm petroleum ether, as in the other organic solvents, it is easily soluble. With acids it gives neutral salts which are easily soluble in water.
The new connection is intended to be used for therapeutic purposes. <I> Example: </I> To a solution of 1.3 parts of asymmetric diethyl-1,8-propylenediamine in 45 parts of 10% sodium hydroxide solution, a benzene solution of 2 is gradually added while stirring and continuously stirring. 2 parts of 2-chloro-4-ebinolincarbonsäurecblorid to.
After the reaction has ended, the benzene solution is separated off, the base formed is extracted with hydrochloric acid and reprecipitated with soda. The base is taken up in ether, the solvent is driven off and it is recrystallized from petroleum ether. The 2-chloro-4-quinolinecarboxylic acid - diethyl -1,3 - propylenediamide forms colorless, leafy crystals with a melting point of 72 0. The base is easily soluble in most organic solvents; with acids it forms neutral, water-soluble salts.
16.7 parts of 2-chloro-4-quinolinecarboxylic acid diethyl-1,3-propylenediamide are boiled with a solution of 1.3 parts of sodium in butyl alcohol. The butyl alcohol is then distilled off, the residue is taken up in ether and washed with water. After removing the solvent, the 2-n-butyloxy-4-quinolinecarboric acid diethyl-1,3-propylenediamide remains as an oil, which soon solidifies to form colorless crystals. The base can be recrystallized from petroleum ether.
Instead of a solution of alkali metal in butyl alcohol, other agents which are used to introduce the butyloxy group can also be used, for example alkali hydroxide in butyl alcohol.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH137338T | 1931-12-21 | ||
CH157849T | 1931-12-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH157849A true CH157849A (en) | 1932-10-15 |
Family
ID=25712965
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH157849D CH157849A (en) | 1931-12-21 | 1931-12-21 | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH157849A (en) |
-
1931
- 1931-12-21 CH CH157849D patent/CH157849A/en unknown
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CH157849A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH157848A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139427A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH137338A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139425A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139424A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139446A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139447A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH157850A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139423A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139440A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139422A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139426A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139428A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139421A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139449A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139450A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139430A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139431A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139437A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH140619A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139429A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139448A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139442A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. | |
CH139443A (en) | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. |