CH139425A - 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.

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Publication number
CH139425A
CH139425A CH139425DA CH139425A CH 139425 A CH139425 A CH 139425A CH 139425D A CH139425D A CH 139425DA CH 139425 A CH139425 A CH 139425A
Authority
CH
Switzerland
Prior art keywords
quinolinecarboxylic acid
preparation
carboxylic acid
petroleum ether
basic derivative
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH139425A publication Critical patent/CH139425A/en

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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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines basischen Derivates einer substituierten       Ciiinolinearbonsäure.       Es wurde gefunden, dass man zu     einem     basischen Derivat einer substituierten     Chi-          nolinca.rbonsäure    gelangt, wenn man auf       Säurehalogenide    der     2-Halogen-4-ehinolin-          carbonsäure    asymmetrisches     Diäthyläthylen-          diamin    einwirken     lä.sst    und das erhaltene     2-          Halogen    -     4-chinolincarb:

  onsäu,re    -     diäthyläthy-          lendia.mid    mit alkalischen Mitteln, die zur       Einführung    der primären     Iso-butyloxygruppe     dienen, umsetzt.  



  Das     2-Iso-butyloxy-4-chinolincarbonsäure-          diäthyläthylendiamid    bildet farblose     Ks-i-          stalle    vom     Schmelzpunkt   <B>73'.</B> Die Base ist  in kaltem     Petroläther    schwer löslich; in war  mem     Petroläther,        wie    in den übrigen orga  nischen Lösungsmitteln ist :sie leicht löslich.  Mit .Säuren gibt sie neutrale,     in.    Wasser  leicht lösliche Salze.  



  Die neue     Verbindung    soll zu therapeu  tischen Zwecken     Verwendung    finden.       Beispiel:     Zu einer Lösung von 1,2 Teilen asymme  trischem     Diäthyläthylendiamin    in 45 Teilen    10     %        iger    Natronlauge     gibt    man unter Küh  lung und ständigem Umrühren allmählich  eine     benzolische    Lösung von 2',2 Teilen 2  Chlor-4-chinolincarbonsäurechlorid zu. Nach       beendigter    Reaktion wird die     benzolische    Lö  sung abgetrennt, die gebildete Base mit  Salzsäure ausgezogen und mit Soda wieder  ausgefällt.

   Man nimmt die Base in Äther  auf,     vertreibt    das Lösungsmittel und kri  stallisiert sie aus     Petroläther    um. Das 2       Chlor-4-chinolincarbonsäure-diäthyläthylen-          diamid    bildet farblose,     blätterige        Kristalle     vom Schmelzpunkt 74'. In den meisten or  ganischen Lösungsmitteln ist die Base leicht  löslich; mit Säuren bildet sie neutrale, was  serlösliche Salze.  



  12 Teile     2-Chlor-4-chinolinca@rbonsäure-          diäthyläthylendiamid    werden     mit    einer Lö  sung von 1 Teil Natrium in primärem     Iso-          butjalkohol    gekocht. Hierauf wird der     Iso-          butylalkohol        abdestilliert,    der Rückstand in  Äther aufgenommen und mit Wasser ge  waschen.

   Nach Entfernung des Lösungs-      mittels verbleibt das     2-Iso-butyloxy-4-chino-          lincarbonsäure-diäthyläthylendiamid    als Öl,  das alsbald zu farblosen     Kristallen        erstarrt.     Die Base lässt sich aus     Petrodäther        um-          kristallisieren.     



  Zur Einführung der primären     Iso-butyl-          oxygruppe    können auch andere     Metall-iso-          butylate    in organischen     Lösungsmitteln    oder  zum Beispiel auch Alkalien in Gegenwart  von     Iso-butylalkohol    Verwendung finden.



  Process for the preparation of a basic derivative of a substituted Ciiinolinearbonsäure. It has been found that a basic derivative of a substituted quinoline carboxylic acid is obtained if asymmetric diethylethylene diamine is allowed to act on acid halides of 2-halo-4-ehinoline carboxylic acid and the 2-halogen-4- quinoline carb:

  onsäu, re - diethyläthy- lendia.mid with alkaline agents that serve to introduce the primary isobutyloxy group.



  The 2-iso-butyloxy-4-quinolinecarboxylic acid diethylethylenediamide forms colorless Ks-i- stalle with a melting point of <B> 73 '. </B> The base is sparingly soluble in cold petroleum ether; in war mem 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. Example: 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-quinolinecarboxylic 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 reprecipitated with soda.

   The base is taken up in ether, the solvent is driven off and it is crystallized from petroleum ether. The 2-chloro-4-quinolinecarboxylic acid diethylethylene diamide forms colorless, leafy crystals with a melting point of 74 '. The base is easily soluble in most organic solvents; with acids it forms neutral, water-soluble salts.



  12 parts of 2-chloro-4-quinolinca @ rboxylic acid diethylethylenediamide are boiled with a solution of 1 part of sodium in primary isobutyl alcohol. The isobutyl alcohol is then distilled off, the residue is taken up in ether and washed with water.

   After removing the solvent, the 2-iso-butyloxy-4-quinolinecarboxylic acid diethylethylenediamide remains as an oil, which soon solidifies to form colorless crystals. The base can be recrystallized from petroleum ether.



  Other metal isobutylates in organic solvents or, for example, alkalis in the presence of isobutyl alcohol can also be used to introduce the primary isobutyl oxy group.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten ;Chinolincar- bonsäure, dadurch gekennzeichnet, dass man auf Säurehalogenide der 2-Halogen-4-chino- lincarbonsäure asymmetrisches Diäthyläthy- lendiamin einwirken lässt und das erhaltene 2-Halogen-4-chinolincarbonsäure-diäthyläthy - lendiamid mit alkalischen Mitteln, PATENT CLAIM: Process for the preparation of a basic derivative of a substituted quinolinecarboxylic acid, characterized in that asymmetric diethylethylenediamine is allowed to act on acid halides of 2-halo-4-quinolinecarboxylic acid and the 2-halo-4-quinolinecarboxylic acid diethylethyl obtained is allowed to act - lendiamide with alkaline agents, die zur Einführung der primären Iso-butyloxy- gruppe dienen, umsetzt. Das 2-Iso-butyloxy-4-chinolincarbonsäure- diäthyläthylendiamid bildet farblose Kri stalle vom Schmelzpunkt<B>73'.</B> Die Base ist in kaltem Petro.läther schwer löslich; in war mem Petroläther, wie in den übrigen orga nischen Lösungsmitteln ist sie leicht löslich. Mit Säuren gibt sie neutrale, in Wasser leicht lösliche Sälze. Die neue Verbindung soll zu therapeu tischen Zwecken Verwendung finden. which are used to introduce the primary isobutyloxy group, converts. The 2-iso-butyloxy-4-quinolinecarboxylic acid diethylethylenediamide forms colorless crystals with a melting point of 73 '. The base is sparingly soluble in cold petroleum ether; In war mem petroleum ether, as in the other organic solvents, it is easily soluble. With acids it gives neutral salts that are easily soluble in water. The new connection is intended to be used for therapeutic purposes.
CH139425D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139425A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139425T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139425A true CH139425A (en) 1930-04-15

Family

ID=25712935

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139425D CH139425A (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) CH139425A (en)

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