CH157849A - 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
CH157849A
CH157849A CH157849DA CH157849A CH 157849 A CH157849 A CH 157849A CH 157849D A CH157849D A CH 157849DA CH 157849 A CH157849 A CH 157849A
Authority
CH
Switzerland
Prior art keywords
diethyl
acid
preparation
quinolinecarboxylic acid
propylenediamide
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 CH157849A publication Critical patent/CH157849A/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     Chino-          lincarbonsäure    gelangt, wenn man auf Säure  halogenide der     2-Halogen-4-chinolincarbon-          säure    asymmetrisches     Diäthyl-1,3-propylen-          diamin    einwirken lässt und das erhaltene  2 -     Halogen-4-chinolincarbonsäure-        diäthyl-1,3-          propylendiamid    mit alkalischen Mitteln,

   die  zur Einführung der     Butyloxygruppe    dienen,  umsetzt.  



  Das     2-n-Butyloxy-4-chinolincarbonsäure-          diäthyl-1,3-propylendiamid    bildet farblose  Kristalle vom Schmelzpunkt<B>630.</B> Die Base  ist in kaltem     Petroläther    schwer löslich; in  warmem     Petroläther,    wie in den übrigen  organischen Lösungsmitteln ist sie leicht lös  lich.     lUit    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 asymme  trischem     Diäthyl-1,8-propylendiamin    in 45 Tei-         len    10      /oiger    Natronlauge gibt man unter  Kühlung und ständigem Umrühren allmäh  lich eine     benzolische    Lösung von 2,2 Teilen       2-Chlor-4-ebinolincarbonsäurecblorid    zu.

   Nach  beendigter 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 kristalli  siert sie aus     Petroläther    um. Das     2-Chlor-4-          chinolincarbonsäure    -     diäthyl    -1,3 -     propylendi-          amid    bildet farblose, blättrige Kristalle vom  Schmelzpunkt 72 0. In den meisten organischen  Lösungsmitteln ist die Base leicht löslich;  mit Säuren bildet sie neutrale, wasserlösliche  Salze.  



  16,7 Teile     2-Chlor-4-chinolincarbonsäure-          diäthyl-1,3-propylendiamid    werden mit einer  Lösung von 1,3 Teilen Natrium in     Butyl-          alkohol    gekocht. Hierauf wird der     Butylal-          kohol        abdestilliert,    der Rückstand in Äther  aufgenommen und mit Wasser gewaschen.  Nach Entfernung des Lösungsmittels verbleibt      das     2-n-Butyloxy-4-chinolincarborrsäure-di-          äthyl-1,3-propylendiamid    als Öl, das alsbald  zu farblosen Kristallen erstarrt. Die Base  lässt sich aus     Petroläther        umkristallisieren.     



  An Stelle einer Lösung von     Alkalimetall     in     Butylalkohol    können auch andere Mittel,  die zur Einführung der     Butyloxygruppe    die  nen, Verwendung finden, zum Beispiel Alkali  hydroxyd in     Butylalkohol.  



  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 diethyl-1,3-propylenediamine is allowed to act on acid halides of 2-halo-4-quinolinecarboxylic acid and the 2-halogen obtained is allowed to act -4-quinolinecarboxylic acid diethyl-1,3-propylenediamide with alkaline agents,

   which serve to introduce the butyloxy group, converts.



  The 2-n-butyloxy-4-quinolinecarboxylic acid diethyl-1,3-propylenediamide forms colorless crystals with a melting point of <B> 630. </B> 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 which are easily soluble in water.



  The new connection is intended to be used for therapeutic purposes. <I> Example: </I> To a solution of 1.3 parts of asymmetric diethyl-1,8-propylenediamine in 45 parts of 10% sodium hydroxide solution, a benzene solution of 2 is gradually added while stirring and continuously stirring. 2 parts of 2-chloro-4-ebinolincarbonsäurecblorid 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 - diethyl -1,3 - propylenediamide forms colorless, leafy crystals with a melting point of 72 0. The base is easily soluble in most organic solvents; with acids it forms neutral, water-soluble salts.



  16.7 parts of 2-chloro-4-quinolinecarboxylic acid diethyl-1,3-propylenediamide are boiled with a solution of 1.3 parts of sodium in butyl alcohol. The butyl alcohol is then distilled off, the residue is taken up in ether and washed with water. After removing the solvent, the 2-n-butyloxy-4-quinolinecarboric acid diethyl-1,3-propylenediamide 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 butyl alcohol, other agents which are used to introduce the butyloxy group can also be used, for example alkali hydroxide in butyl alcohol.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolincarbon- säure, dadurch gekennzeichnet, dass man auf Säurehalogenide der 2-Halogen-4-chinolincar- bonsäure asymmetrisches Diäthyl-1,3-propy- endiamin einwirken lässt und das erhaltene 2 -Halogen-4-chinolincarbonsäure - diäthyl-1,3- propylendiamid mit alkalischen Mitteln, die zur Einführung der Butyloxygruppe dienen, umsetzt. Claim: Process for the preparation of a basic derivative of a substituted quinolinecarboxylic acid, characterized in that asymmetric diethyl-1,3-propylene diamine is allowed to act on acid halides of 2-halo-4-quinolinecarboxylic acid and the 2 -halogen- 4-quinolinecarboxylic acid - diethyl-1,3-propylenediamide with alkaline agents that serve to introduce the butyloxy group, reacts. Das 2-n-Butyloxy-4-chinolincarbonsäLire- diäthyl -1,3 - propylendiamid bildet farblose Kristalle vom Schmelzpunkt<B>63'.</B> Die Base ist in kaltem Petroläther schwer löslich; in warmem Petroläther, wie in den übrigen organischen Lösungsmitteln ist sie leicbt lös lich. Mit Säuren gibt sie neutrale, in Wasser leicht lösliche Salze. Die neue Verbindung soll zu therapeuti schen Zwecken Verwendung finden. The 2-n-butyloxy-4-quinolincarboxylic acid diethyl -1,3-propylenediamide forms colorless crystals with a melting point of <B> 63 '. </B> 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.
CH157849D 1931-12-21 1931-12-21 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH157849A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH137338T 1931-12-21
CH157849T 1931-12-21

Publications (1)

Publication Number Publication Date
CH157849A true CH157849A (en) 1932-10-15

Family

ID=25712965

Family Applications (1)

Application Number Title Priority Date Filing Date
CH157849D CH157849A (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) CH157849A (en)

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