CH139448A - 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
CH139448A
CH139448A CH139448DA CH139448A CH 139448 A CH139448 A CH 139448A CH 139448D A CH139448D A CH 139448DA CH 139448 A CH139448 A CH 139448A
Authority
CH
Switzerland
Prior art keywords
acid
preparation
carboxylic acid
quinoline carboxylic
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 CH139448A publication Critical patent/CH139448A/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)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung eines basischen Derivates einer substituierten       Cliinolincarbonsäure.       Es wurde     gefunden,    dass man zu einem  basischen Derivat einer substituierten     Chino-          lincarbonsäure        gelangt,

      wenn man auf Säure       ha.logenide    der     2-Halogen-4-chinolincarbon-          säure    asymmetrisches     n-Dibutyläthylendi-          amin        einwirken    lässt     und    das erhaltene     2-          Halogen    - 4 -     ,chinolincarbonsäure    - n -     dibutyl        -          äthylendiamid    mit alkalischen     Äthoxylie-          rungsmitteln        umsetzt.     



  Das     2-Äthoxy-d--chinolincarbonsäure-n-di-          butyl.äthylenclia-rriid    bildet farblose     Krista:l'e     vom     Schmelzpunkt    51,5  . Die Base lässt sich  aus     Petroläther        umkristallisieren.    Mit Säuren  bildet sie neutrale, wasserlösliche Salze.  



  Die neue Verbindung soll zu therapeu  tischen     Z@N=eckeri        Verwendung        finden.     <I>Beispiel:</I>       Zu    einer Lösung von 3,5 Teilen asym  metrischem     n-Dibutyläthylendiamin    in<B>90</B>       Teilen    10 %     iger        Natronlauge    gibt man unter  Kühlung     und    ständigem     Umrühren    allmäh-         lich    eine     benzolische    Lösung von 4,4 Teilen       2-Chlor-4-chinolincarbonsäurechlorid    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-Chl,or-4-chino-          liucarbonsäure-n-dibutyläthylen.dia.mid    bildet  farblose Kristalle vom     Schmelzpunkt    59     '.     In     den    meisten organischen Lösungsmitteln  ist die Base leicht löslich; mit 'Säuren     bildet     sie neutrale, wasserlösliche Salze.  



  Das     n-Dibutyläthylendiamin        (-S.d'p.    12  <B>931</B> wird durch Reduktion von     n-Dibu-          tylamino:a.cetonitril    mit Natrium und<B>Alko-</B>  hol erhalten. Das     n-Dibutyl-amino@a.cetonitril          (.SdP.    12 113  )     entsteht    ,bei ;der     Kondensation     von     Formaldehyd    mit Blausäure und     n-Di-          butyla,min.     



  18 Teile     2-Chlor-4-ähinolincarbonsäure        n-          clibutyläthylendiamid    werden mit einer Lö-           sunb    von 1,3 Teilen Natrium in Äthylalko  hol     bekocht.    Hierauf wird der     Äthylalkohol          abdestilliert,        Jer        1@Lüclistand    in Äther     auf-          ben0mmen    und mit Wasser "waschen.

   Nach  Entfernung des     Lösungsmittels    verbleibt  das     2-Äthoxv-4-chinolinca.rbonsäure-n-,dibii-          tyläthylendia.mid    .als farblose Kristalle; die  Base lässt sich aus     Petroläther        umkristalli-          sieren.     



       Zur    Einführung der     Äthoxyb        uppe    kön  nen auch andere     M.etalläihylate    in organi  schen Lösungsmitteln oder zum Beispiel auch       Alkalien    in Gegenwart von     Äthyl.alkoliol          Verwendung    finden.



  Process for the preparation of a basic derivative of a substituted cliinoline carboxylic acid. It has been found that a basic derivative of a substituted quinoline carboxylic acid is obtained,

      if asymmetric n-dibutylethylenediamine is allowed to act on acid ha.logenide of 2-halo-4-quinolinecarboxylic acid and the 2-halo-4-quinolinecarboxylic acid-n-dibutyl-ethylenediamide is reacted with alkaline ethoxylating agents.



  The 2-ethoxy-d-quinolincarboxylic acid-n-di-butyl.äthylenclia-rriid forms colorless crystals with a melting point of 51.5. The base can be recrystallized from petroleum ether. With acids it forms neutral, water-soluble salts.



  The new connection should be used for therapeutic Z @ N = eckeri. <I> Example: </I> A solution of 3.5 parts of asymmetrical n-dibutylethylenediamine in 90 parts of 10% sodium hydroxide solution is gradually added to a solution of benzene with cooling and constant stirring 4.4 parts of 2-chloro-4-quinolinecarboxylic acid chloride.

   After the reaction has ended, the benzene solution is separated off, and the base formed with. Hydrochloric acid extracted and precipitated out again with soda. The base is taken up in ether, the solvent is driven off and it is recrystallized from petroleum ether.

   The 2-Chl, or-4-quino-liucarboxylic acid-n-dibutylethylene.dia.mid forms colorless crystals with a melting point of 59 '. The base is easily soluble in most organic solvents; with acids it forms neutral, water-soluble salts.



  The n-dibutylethylenediamine (-S.d'p. 12 <B> 931 </B> is obtained by reducing n-dibutylamino: a.cetonitrile with sodium and <B> alcohol n-Dibutyl-amino@a.cetonitrile (.SdP. 12 113) is formed during the condensation of formaldehyde with hydrocyanic acid and n-dibutyla, min.



  18 parts of 2-chloro-4-ähinolinecarboxylic acid n-clibutylethylenediamide are cooked with a solution of 1.3 parts of sodium in ethyl alcohol. The ethyl alcohol is then distilled off, soak Jer 1 @ Lüclistand in ether and wash with water.

   After removal of the solvent, the 2-ethoxy-4-quinolinca.rboxylic acid-n-, dibiityläthylendia.mid .as colorless crystals; the base can be recrystallized from petroleum ether.



       To introduce the Äthoxybuppe NEN other M.etalläihylate in organic solvents or, for example, alkalis in the presence of Äthyl.alkoliol can be used.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basi schen Derivates einer substituierten Chinolin- carbonsäure; tda,durch gekennzeichnet, dar man auf Säurehalogenide der 2-Haloben--1- chinolincarbonsäure asymmetrisches n-Dibiz- l;yläthylen.diamin einwirken lässt und das er haltene 2-Halogen-4-chinolinca.rbonsäure-n- clibutyläthylendiamid mit alkalischenxthoxy- lierunbsmitteln umsetzt. PATENT CLAIM: Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid; tda, characterized by being allowed to act on acid halides of 2-halobes - 1- quinolinecarboxylic acid asymmetric n-dibiz- l; yläthylen.diamin and the 2-halo-4-quinolincarboxylic acid-n-clibutylethylenediamide obtained with alkalinexthoxy implements foodstuffs. Das 2-Äthoxy-4-chinolincarbonsäure-n-di- biityläthylendia.mi,d bildet farblose Kristalle vom Schmelzpunkt 51,5 . Die Base lässt sich aus PetrolUther umkrista.llisieren. Mit Säuren bildet sie neutrale, wasserlösliche -Salze. Die neue Verbindung soll zu therapeu tischen Zwecken Ver-,vendunb finden. The 2-ethoxy-4-quinolincarboxylic acid-n-di-biityläthylendia.mi, d forms colorless crystals with a melting point of 51.5. The base can be recrystallized from petroleum ether. With acids it forms neutral, water-soluble salts. The new connection should be used for therapeutic purposes.
CH139448D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139448A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139448T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139448A true CH139448A (en) 1930-04-15

Family

ID=25712958

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139448D CH139448A (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) CH139448A (en)

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