CH139446A - 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
- CH139446A CH139446A CH139446DA CH139446A CH 139446 A CH139446 A CH 139446A CH 139446D A CH139446D A CH 139446DA CH 139446 A CH139446 A CH 139446A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- acid
- preparation
- quinoline carboxylic
- diethylpropylenediamide
- 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 Basisehen Derivates einer substituierten Chinolincarbonsäure. Es wurde gefunden, dass man zu einem basischen Derivat einer substituierten Chino- lincarbonsäure gelangt, wenn man auf Säure halogenide der 2-Halogen-4-ehinolincarbon- säure Diäthylpropylendiämin der Formel
EMI0001.0007
einwirken lässt und das erhaltene 2-Halogen- 4 - chinolincarbonsäure - diäthylpropylendiamid mit alkalischen Äthogylierungsmitteln um setzt.
Das 2-Äthogy-4-chinolincarbonsäure-di- äthylpropylendiamid bildet farblose Kristalle vom Schmelzpunkt 740. Die Base ist in kaltem 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 1,3 Teilen Diäthyl- propylendiamin in 45 Teilen 10 %iger Natron lauge gibt man unter Kühlung und ständigem Umrühren allmählich eine benzolische Lösung von 2,2 Teilen 2-Chlor-4-chinolinoarbonsäure- chlorid zu. Nach beendigter Reaktion wird die benzolische Lösung abgetrennt, die ge bildete Base mit Salzsäure ausgezogen und mit Soda wieder ausgefällt. Man nimmt die Base in Äther auf, vertreibt das Lösungs mittel und kristallisiert sie aus Petroläther um.
Das 2-Chlor-4-chinolincarbonsäure-diäthyl- propylendiamid bildet farblose, blätterige Kri stalle vom Schmelzpunkt 66 0. In den meisten organischen Lösungsmitteln ist die Base leicht löslich; mit Säuren bildet sie neutrale, wasser lösliche Salze.
Das asymmetrische Diäthylpropylendiamin (Siedepunkt 162 0) wird bei der Reduktion von Diäthylaminopropionitril mit Natrium und Alkohol erhalten. Das Nitril (Sdp. 20 80 ) bildet sich bei der Kondensation von Acetaldehyd mit Blausäure und Diäthylamin.
32 Teile 2-Chlor-4-chinolincarbonsäure- diäthylpropylendiamid werden mit einer Lö sung von 2,6 Teilen Natrium in Äthylalkohol gekocht. Hierauf wird der Äthylalkohol ab destilliert, der Rückstand in Äther aufge nommen und mit Wasser gewaschen. Nach Entfernung des Lösungsmittels verbleibt das 2-Äthoxy-4-chinolincarbonsäLlre-diäthylpropy- lendiamid als farblose Kristalle, die aus Pe- troläther umkristallisiert werden können.
Zur Einführung der Äthoxygruppe können auch andere Metalläthylate in organischen Lösungsmitteln oder zum Beispiel auch Al- kalien in Gegenwart von Äthylalkohol Ver wendung finden.
Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. It has been found that a basic derivative of a substituted quinoline carboxylic acid is obtained when acid halides of the 2-halo-4-ehinoline carboxylic acid diethylpropylenediamine of the formula are used
EMI0001.0007
can act and the resulting 2-halo 4 - quinoline carboxylic acid - diethylpropylenediamide with alkaline ethogylating agents.
The 2-ethogy-4-quinolinecarboxylic acid diethylpropylenediamide forms colorless crystals with a melting point of 740. 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 1.3 parts of diethylpropylenediamine in 45 parts of 10% sodium hydroxide solution, a benzene solution of 2.2 parts of 2-chloro-4- is gradually added with cooling and constant stirring quinolinoarboxylic acid chloride 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 diethylpropylenediamide forms colorless, leafy crystals with a melting point of 66 0. The base is easily soluble in most organic solvents; with acids it forms neutral, water-soluble salts.
The asymmetrical diethylpropylenediamine (boiling point 162 0) is obtained in the reduction of diethylaminopropionitrile with sodium and alcohol. The nitrile (bp. 20 80) is formed during the condensation of acetaldehyde with hydrocyanic acid and diethylamine.
32 parts of 2-chloro-4-quinolincarboxylic acid diethylpropylenediamide are boiled with a solution of 2.6 parts of sodium in ethyl alcohol. Then the ethyl alcohol is distilled off, the residue taken up in ether and washed with water. After the solvent has been removed, the 2-ethoxy-4-quinoline-carboxylic acid diethylpropylene diamide remains as colorless crystals which 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 |
---|---|---|---|
CH139446T | 1927-11-19 | ||
CH137338T | 1931-12-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH139446A true CH139446A (en) | 1930-04-15 |
Family
ID=25712956
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH139446D CH139446A (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) | CH139446A (en) |
-
1927
- 1927-11-19 CH CH139446D patent/CH139446A/en unknown
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