CH139422A - 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
CH139422A
CH139422A CH139422DA CH139422A CH 139422 A CH139422 A CH 139422A CH 139422D A CH139422D A CH 139422DA CH 139422 A CH139422 A CH 139422A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
preparation
acid
petroleum ether
substituted quinoline
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 CH139422A publication Critical patent/CH139422A/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       Chinolinearbonsäure.       Es wurde gefunden, dass man zu einem       basischen.    Derivat einer     substituierten        Chi-          nolincarbonsäure    gelangt,

   wenn man auf       Säurehailogenide    der     2-Halogen-4-chinolin-          carbonsäure    asymmetrische     Diäthyläthylen-          diamin    einwirken lässt und     dass    erhaltene 2  Ha.l     ogen-    4 -     chinolincarb        onsäure-        diäthyläthy-          lendiamid    mit alkalischen     Mitteln,    die zur       Einführung    der     n-Propyloxygi-nppe    dienen,  umsetzt.  



  Das     2-n-Propyloxy-4-chinolincarbonsäure-          diäthyläthylendiamid    bildet farblose Kri  stalle vom Schmelzpunkt 63  . Die Base     i'st     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.  <I>Beispiel:</I>  Zu einer     Lösung    von 1,2 Teilen asymme  trischem     Diäthyläthylendiamin    in 45 Teilen    1.0 %     iger    Natronlauge     gibt    man unter Küh  lung und     ständigem        Umrühren        allmählich     eine     benzalische    Lösung von 2,2 Teilen 2  Chlor-4-ehinolincarbomäurechlorid zu. Nach  beendigter Reaktion wird die     benzolische    Lö  sung abgetrennt, die gebildete Base mit Salz  säure ausgezogen und mit Soda wieder aus  gefällt.

   Man nimmt :die Base in Äther auf,  vertreibt     das    Lösungsmittel und     kristallisiert     sie aus     Petroläther    um. Das     2-Chlor-4-chi-          nolincarbonsäure-diäthyläthyäendiamid    bildet  farblose,     blättrige        Kristalle    vom Schmelz  punkt 74'. In den meisten organischen Lö  sungsmitteln     ist    die Base leicht löslich; mit  Säuren bildet sie neutrale, wasserlösliche  Salze.  



  30 Teile     2-Chlor-4-chinolinca.rbonsäure-          diäthyläthylendiamid    werden mit einer Lö  sung von 2,3 Teilen Natrium in     n-Propyl-          alkohol    gekocht. Hierauf wird der     n-Propyl-          alkohol        abdestikiert,    der Rückstand in Äther  aufgenommen und mit Wasser gewaschen.

    Nach     Entfernung    des     Lösungsmittels    ver-      bleibt das     2-n-Propyloxy-4-chinolinearbon-          säure-diäthyläthylendia.mid    als Öl, das als  bald zu farblosen Kristallen     erstarrt..    Die  Base lässt sich aus     Petroläther        umkristalli-          sieren.     



  Zur Einführung der     n-Propyloxygruppe     können auch andere     Metall-n-propylate    in or  ganischen Lösungsmitteln oder zum Beispiel  auch Alkalien in     Gegenwart    von     n-Propyl-          alkohol    Verwendung finden.



  Process for the preparation of a basic derivative of a substituted quinolinearboxylic acid. It was found that one becomes a basic one. Derivative of a substituted quinolinecarboxylic acid,

   when asymmetric diethylethylene diamine is allowed to act on acid halides of 2-halo-4-quinoline-carboxylic acid and the 2 halo-4-quinoline-carbonic acid diethylethylene diamide obtained with alkaline agents that lead to the introduction of n-propyloxygi-nppe serve, implement.



  The 2-n-propyloxy-4-quinolincarboxylic acid diethylethylenediamide forms colorless crystals with a melting point of 63. 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 that are easily soluble in water.



  The new connection should be used for therapeutic purposes. <I> Example: </I> To a solution of 1.2 parts of asymmetric diethylethylenediamine in 45 parts of 1.0% sodium hydroxide solution, a benzalic solution of 2.2 parts of 2-chloro-4-ehinoline carbomic acid chloride is gradually added with cooling and constant stirring to. After the reaction has ended, the benzene solution is separated off, the base formed is extracted with hydrochloric acid and precipitated again with soda.

   You take up: the base in ether, drive off the solvent and recrystallize it from petroleum ether. The 2-chloro-4-quinolinecarboxylic acid diethyläthyäendiamid forms colorless, leafy crystals with a melting point of 74 '. The base is readily soluble in most organic solvents; with acids it forms neutral, water-soluble salts.



  30 parts of 2-chloro-4-quinolinca.rboxylic acid diethylethylenediamide are boiled with a solution of 2.3 parts of sodium in n-propyl alcohol. The n-propyl alcohol is then distilled off, the residue is taken up in ether and washed with water.

    After removing the solvent, the 2-n-propyloxy-4-quinolinearboxylic acid diethylethylenedia.mid remains as an oil, which soon solidifies as colorless crystals. The base can be recrystallized from petroleum ether.



  Other metal n-propylates in organic solvents or, for example, alkalis in the presence of n-propyl alcohol can also be used to introduce the n-propyloxy group.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolinca,r- bonsäure, dadurch gekennzeichnet, dass man auf Säurehalo"-,enide.der2,--Halogen-4-chinolin- carbonsäure asymmetrisches Diäthyläthylen- diamin einwirken lässt und das erhaltene 2-Halogen-4-chinolincarbonsäurediäthyläthy- lendiamid mit alkalischen Mitteln, die zur Einführung der n-Propylgruppe dienen, um setzt. PATENT CLAIM: A process for the preparation of a basic derivative of a substituted quinoline, r- bonsäure, characterized in that one lets act on acid halo "-, enide.der2, - halogen-4-quinoline-carboxylic acid asymmetrical diethylethylene diamine and the 2- Halogen-4-quinolincarbonsäurediäthyläthy- lendiamid with alkaline agents which serve to introduce the n-propyl group to sets. Das 2-n-Propyloxy-4-ehinolincarbonsäure- diäthyläthylendiamid bildet farblose Kri stalle vom Schmelzpunkt<B>63'.</B> Die Base ist in kaltem Petroläther schwer löslich; in war mem Petrolä-ther, 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. The 2-n-propyloxy-4-ehinoline-carboxylic acid diethylethylenediamide forms colorless crystals with a melting point of <B> 63 '. </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, easily soluble salts in water. The new connection is intended to be used for therapeutic purposes.
CH139422D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139422A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139422T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139422A true CH139422A (en) 1930-04-15

Family

ID=25712932

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139422D CH139422A (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) CH139422A (en)

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