CH139440A - 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
CH139440A
CH139440A CH139440DA CH139440A CH 139440 A CH139440 A CH 139440A CH 139440D A CH139440D A CH 139440DA CH 139440 A CH139440 A CH 139440A
Authority
CH
Switzerland
Prior art keywords
acid
preparation
quinolinecarboxylic 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 CH139440A publication Critical patent/CH139440A/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)
  • Quinoline Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines basischen Derivates einer substituierten       Chinolinearbonsäure.       Es     wurde    gefunden,     da.B    man zu einem  basischen Derivat einer     substituierten        Chi-          nolincarbonsäure        gelangt,    wenn man     auf          Säurehalogenide    der     2-Halogen-4-chinolin-          carbonsäure    asymmetrisches     Diäthylpenta-          methylendiamin    der     Formel          (C2H5)2    N .

       C112    .     CH2    .     CH2    .     CH2    .     C112        #        NH2     einwirken     läBt    und das erhaltene     2-Halogen-          4    -     chinolincarbonsäure-diäthylpentamethylen-          diamid    mit alkalischen     Athoxylierungsmit-          teln    umsetzt.  



  Das     2-Äthoxy-4-chinolincarbonsäure-di-          äthylpentamethylendiamid    bildet farblose  Kristalle vom Schmelzpunkt 74'. Die Base  ist 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.         Beispiel:     Zu einer Lösung von 1,6 Teilen asymme  trischem     Diäthylpentamethylendiamin    in 45  Teilen 10%iger Natronlauge gibt man unter  Kühlung und ständigem Umrühren allmäh  lich eine     benzolische    Lösung von 2,2 Teilen       2-Chlor-4-c-hino#lincarbonsäurechlorid    zu. Nach  beendigter     Reaktion    wird die     benzolische    Lö  sung abgetrennt, die gebildete Base mit Salz  säure ausgezogen und mit Soda ausgefällt.

    Man nimmt die Base in Äther auf, vertreibt  das     Lösungsmittel    und kristallisiert sie aus       Petroläther    um. Das     2-Chlor-4-chinolincar-          bonsäure-diäthylpentamethylendiamid    bildet  farblose, blättrige Kristalle vom Schmelz  punkt 55  . In den     meisten    organischen Lö  sungsmitteln ist die Base leicht löslich; mit  Säuren bildet sie neutrale,     wasserlösliche     Salze.  



  17 Teile     2-Chlor-4-,ehinolincarb.onsätire-di-          äthylpentamethylendiamid    werden mit einer  Lösung von 1,5 Teilen Natrium in Äthyl-           alkohol    gekocht. Hierauf wird der     Äthyl-          alkohol        abdestilliert,    der Rückstand in Äther  aufgenommen und mit Wasser gewaschen.  Nach Entfernung des     Lösungsmittels    ver  bleibt das     2-Äthoxy-4-chinolincarbonsäure-          diäthylpentamethylendiamid    als Öl, das     aIs-          ba.ld    zu farblosen     Kristallen    erstarrt.

   Die  Base lässt sich aus     Petroläther        umkristalli-          sieren.     



  Zur Einführung der     Äthoxygruppe    kön  nen     aueh    andere     Metalläthylate    in orga  nischen Lösungsmitteln oder zum Beispiel  auch Alkalien in     Gegenwaa-t    von     Äthylalko-          hol    Verwendung finden.



  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 diethylpentamethylene diamine of the formula (C2H5) 2N is used on acid halides of 2-halo-4-quinolinecarboxylic acid.

       C112. CH2. CH2. CH2. C112 # NH2 can act and the resulting 2-halo-4-quinolinecarboxylic acid diethylpentamethylene diamide is reacted with alkaline ethoxylating agents.



  The 2-ethoxy-4-quinolinecarboxylic acid diethylpentamethylene diamide forms colorless crystals with a melting point of 74 '. 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. Example: To a solution of 1.6 parts of asymmetric diethylpentamethylenediamine in 45 parts of 10% sodium hydroxide solution, a benzene solution of 2.2 parts of 2-chloro-4-c-hino # lincarboxylic 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 precipitated 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 diethylpentamethylene diamide forms colorless, leafy crystals with a melting point of 55. The base is easily soluble in most organic solvents; with acids it forms neutral, water-soluble salts.



  17 parts of 2-chloro-4-, ehinolincarb.onsätire-diethylpentamethylendiamid are boiled with a solution of 1.5 parts of sodium in ethyl alcohol. The ethyl alcohol is then distilled off, the residue is taken up in ether and washed with water. After removing the solvent, the 2-ethoxy-4-quinolinecarboxylic acid diethylpentamethylenediamide remains as an oil, which solidifies as aIs- ba.ld to form colorless crystals.

   The base 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)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolinear- bonsäure, dadurch gekennzeichnet, dass man auf Säurehalogenide der 2-Halogen-4-chino- lincarbonsäure asymmetrisches Diäthylpent.a- rnethylendia.min der Formel (C2H5) PATENT CLAIM: Process for the preparation of a basic derivative of a substituted quinolinearboxylic acid, characterized in that asymmetric diethylpent.arnethylenedia.min of the formula (C2H5) is based on acid halides of the 2-halo-4-quinolinecarboxylic acid 2 N # CH2 # CH2 # CH_ # <B>CH?</B> # CH2 # NH2 einwirken läBt und das erhaltene 2-Halogen- 4-chinolincarbonsäure- diäthylpentamethy len- diamid mit alkalischen Äthoxylierungs- mitteln umsetzt. 2 N # CH2 # CH2 # CH_ # <B> CH? </B> # CH2 # NH2 can act and the resulting 2-halo-4-quinolinecarboxylic acid diethylpentamethylene diamide is reacted with alkaline ethoxylating agents. Das 2-Ätho.xy-4-chinolincarbonsäure-di- äthylpenta.methylendiamid bildet farblose Kristalle vom Schmelzpunkt 74'. Die Base ist 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 Wasser leicht lösliche Salze. Die neue Verbindung soll zu therapeu tischen Zwecken Verwendung finden. The 2-Ätho.xy-4-quinolinecarboxylic acid-diethylpenta.methylendiamid forms colorless crystals with a melting point of 74 '. 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.
CH139440D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139440A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139440T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139440A true CH139440A (en) 1930-04-15

Family

ID=25712950

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139440D CH139440A (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) CH139440A (en)

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