CH139440A - 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
- CH139440A CH139440A CH139440DA CH139440A CH 139440 A CH139440 A CH 139440A CH 139440D A CH139440D A CH 139440DA CH 139440 A CH139440 A CH 139440A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- preparation
- quinolinecarboxylic acid
- petroleum ether
- basic derivative
- 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
Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolinearbonsäure. Es wurde gefunden, da.B man zu einem basischen Derivat einer substituierten Chi- nolincarbonsäure gelangt, wenn man auf Säurehalogenide der 2-Halogen-4-chinolin- carbonsäure asymmetrisches Diäthylpenta- methylendiamin der Formel (C2H5)2 N .
C112 . CH2 . CH2 . CH2 . C112 # NH2 einwirken läBt und das erhaltene 2-Halogen- 4 - chinolincarbonsäure-diäthylpentamethylen- diamid mit alkalischen Athoxylierungsmit- teln umsetzt.
Das 2-Äthoxy-4-chinolincarbonsäure-di- äthylpentamethylendiamid bildet farblose Kristalle vom Schmelzpunkt 74'. Die Base ist in kaltem Petroläther schwer löslich; in warmem Petroläther, wie in den übrigen or ganischen Lösungsmitteln ist sie leicht lös lich. Mit .Säuren gibt sie neutrale, in Was ser leicht lösliche Salze.
Die neue Verbindung soll zu therapeu tischen Zwecken Verwendung finden. Beispiel: Zu einer Lösung von 1,6 Teilen asymme trischem Diäthylpentamethylendiamin in 45 Teilen 10%iger Natronlauge gibt man unter Kühlung und ständigem Umrühren allmäh lich eine benzolische Lösung von 2,2 Teilen 2-Chlor-4-c-hino#lincarbonsäurechlorid zu. Nach beendigter Reaktion wird die benzolische Lö sung abgetrennt, die gebildete Base mit Salz säure ausgezogen und mit Soda ausgefällt.
Man nimmt die Base in Äther auf, vertreibt das Lösungsmittel und kristallisiert sie aus Petroläther um. Das 2-Chlor-4-chinolincar- bonsäure-diäthylpentamethylendiamid bildet farblose, blättrige Kristalle vom Schmelz punkt 55 . In den meisten organischen Lö sungsmitteln ist die Base leicht löslich; mit Säuren bildet sie neutrale, wasserlösliche Salze.
17 Teile 2-Chlor-4-,ehinolincarb.onsätire-di- äthylpentamethylendiamid werden mit einer Lösung von 1,5 Teilen Natrium in Äthyl- alkohol gekocht. Hierauf wird der Äthyl- alkohol abdestilliert, der Rückstand in Äther aufgenommen und mit Wasser gewaschen. Nach Entfernung des Lösungsmittels ver bleibt das 2-Äthoxy-4-chinolincarbonsäure- diäthylpentamethylendiamid als Öl, das aIs- ba.ld zu farblosen Kristallen erstarrt.
Die Base lässt sich aus Petroläther umkristalli- sieren.
Zur Einführung der Äthoxygruppe kön nen aueh andere Metalläthylate in orga nischen Lösungsmitteln oder zum Beispiel auch Alkalien in Gegenwaa-t von Äthylalko- hol Verwendung finden.
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 diethylpentamethylene diamine of the formula (C2H5) 2N is used on acid halides of 2-halo-4-quinolinecarboxylic acid.
C112. CH2. CH2. CH2. C112 # NH2 can act and the resulting 2-halo-4-quinolinecarboxylic acid diethylpentamethylene diamide is reacted with alkaline ethoxylating agents.
The 2-ethoxy-4-quinolinecarboxylic acid diethylpentamethylene diamide forms colorless crystals with a melting point of 74 '. 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, easily soluble salts in water.
The new connection is intended to be used for therapeutic purposes. Example: To a solution of 1.6 parts of asymmetric diethylpentamethylenediamine in 45 parts of 10% sodium hydroxide solution, a benzene solution of 2.2 parts of 2-chloro-4-c-hino # lincarboxylic acid chloride is gradually added with cooling and constant stirring. After the reaction has ended, the benzene solution is separated off, the base formed is extracted with hydrochloric acid and precipitated 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 diethylpentamethylene diamide forms colorless, leafy crystals with a melting point of 55. The base is easily soluble in most organic solvents; with acids it forms neutral, water-soluble salts.
17 parts of 2-chloro-4-, ehinolincarb.onsätire-diethylpentamethylendiamid are boiled with a solution of 1.5 parts of sodium in ethyl alcohol. The ethyl alcohol is then distilled off, the residue is taken up in ether and washed with water. After removing the solvent, the 2-ethoxy-4-quinolinecarboxylic acid diethylpentamethylenediamide remains as an oil, which solidifies as aIs- ba.ld to form colorless crystals.
The base can be recrystallized from petroleum ether.
Other metal ethylates in organic solvents or, for example, alkalis in the presence of ethyl alcohol can also be used to introduce the ethoxy group.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH139440T | 1927-11-19 | ||
CH137338T | 1931-12-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH139440A true CH139440A (en) | 1930-04-15 |
Family
ID=25712950
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH139440D CH139440A (en) | 1927-11-19 | 1927-11-19 | Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH139440A (en) |
-
1927
- 1927-11-19 CH CH139440D patent/CH139440A/en unknown
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