CH157848A - 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
- CH157848A CH157848A CH157848DA CH157848A CH 157848 A CH157848 A CH 157848A CH 157848D A CH157848D A CH 157848DA CH 157848 A CH157848 A CH 157848A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- preparation
- carboxylic 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)
- Plural Heterocyclic 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 Diäthyläthylendiamin einwirken lässt und das erhaltene 2-Halogen- 4 - chinolincarbonsäure - diäthyläthylendiamid mit alkalischen Mitteln, die zur Einführung der Hexyloxygruppe dienen, umsetzt.
Das 2-n-Hexyloxy-4-chinolincarbonsäure- diätbyläthylendiamid bildet farblose Kristalle vom Schmelzpunkt 73 0. Die Base ist in kal tem Petroläther schwer löslich; in warmem Petroläther, wie in den übrigen organischen Lösungsmitteln ist sie leicht löslich. Mit 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 1,2 Teilen asymme trischem Diäthyläthylendiamin in 45 Teilen 10 %iger Natronlauge gibt man unter Küh- lung und ständigem Rühren allmählich eine benzolische Lösung von 2,2 Teilen 2-Chlor- 4-chinolincarbonsäurechlorid zu.
Nach been deter 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 kristallisiert sie aus Petroläther um. Das 2-Chlor-4-chinolincarbon- säure-diäthyläthylendiamid bildet farblose, blättrige Kristalle vom Schmelzpunkt 74'. In den meisten organischen Lösungsmitteln ist die Base leicht lösli(;h; mit Säuren bildet sie neutrale, wasserlösliche Salze.
15 Teile 2-Chlor-4-chinolincarbonsäure- diäthyläthylendiamid werden mit einer Lösung von 1,3 Teilen Natrium in Hexylalkohol ge kocht. Hierauf wird der ri-Hexylalkohol ab destilliert, der Rückstand in Äther aufge nommen und mit Wasser gewaschen. Nach Entfernung des Lösungsmittels verbleibt das 2 - n - Hexyloxy-4-chinolincarbo nsäure - diäthyl- äthylendiamid als Öl, das alsbald zu farb losen Kristallen erstarrt. Die Base lässt sich aus Petroläther umkristallisieren.
An Stelle einer Lösung von Alkalimetall in Hexylalkohol können auch andere Mittel, die zur Einführung der Hexyioxygruppe die nen, Verwendung finden, zum Beispiel Alkali hydroxyd in Hegylalkohol.
Process for the preparation of a basic derivative of a substituted quinolinearboxylic acid. It has been found that a basic derivative of a substituted quinoline carboxylic acid is obtained,
if you can act on acid halides of 2-halo-4-quinolincarboxylic acid asymmetric diethylethylenediamine and the 2-halo-4-quinolinecarboxylic acid - diethylethylenediamide with alkaline agents that serve to introduce the hexyloxy group, is implemented.
The 2-n-hexyloxy-4-quinolincarboxylic acid dietbylethylenediamide forms colorless crystals with a melting point of 73 0. The base is sparingly soluble in cold petroleum ether; It is easily soluble in warm petroleum ether, as in the other organic solvents. With acids it gives neutral, easily soluble salts in water.
The new connection is intended to be used for therapeutic purposes. <I> Example: </I> To a solution of 1.2 parts of asymmetric diethylethylenediamine in 45 parts of 10% sodium hydroxide solution, a benzene solution of 2.2 parts of 2-chloro-4 is gradually added while cooling and with constant stirring -quinoline carboxylic acid chloride too.
After the end of the reaction, 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 diethylethylenediamide forms colorless, leafy crystals with a melting point of 74 '. The base is easily soluble in most organic solvents (; h; with acids it forms neutral, water-soluble salts.
15 parts of 2-chloro-4-quinolincarboxylic acid diethylethylenediamide are boiled with a solution of 1.3 parts of sodium in hexyl alcohol. Then the ri-hexyl alcohol is distilled off, the residue taken up in ether and washed with water. After removal of the solvent, the 2 - n - hexyloxy-4-quinolincarbo nic acid diethyl ethylenediamide 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 hexyl alcohol, it is also possible to use other agents which serve to introduce the hexyioxy group, for example alkali hydroxide in hegyl alcohol.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH137338T | 1931-12-21 | ||
CH157848T | 1931-12-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH157848A true CH157848A (en) | 1932-10-15 |
Family
ID=25712964
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH157848D CH157848A (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) | CH157848A (en) |
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1931
- 1931-12-21 CH CH157848D patent/CH157848A/en unknown
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