CH125406A - Process for the preparation of a substituted quinoline carboxylic acid derivative. - Google Patents

Process for the preparation of a substituted quinoline carboxylic acid derivative.

Info

Publication number
CH125406A
CH125406A CH125406DA CH125406A CH 125406 A CH125406 A CH 125406A CH 125406D A CH125406D A CH 125406DA CH 125406 A CH125406 A CH 125406A
Authority
CH
Switzerland
Prior art keywords
acid derivative
preparation
carboxylic acid
quinolinecarboric
quinoline carboxylic
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 CH125406A publication Critical patent/CH125406A/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)

Description

  

  Verfahren zur Darstellung eines substituierten     Chinolincarbonsäurederivates.       Es wurde gefunden, dass man zu einem  substituierten     Chinolincarbonsäurederivat    ge  langt, wenn     rnan    auf     a-Halogen-r-chirrolirr-          carbonsäurehalogenid        Diäthylamin    einwirken       lä13t    und das erhaltene     a-Halogen-i--chinolin-          car-borrsäur-ediätlrylamid    mit alkalischen     Propy-          lierungsrnitteln,

      wie zurr Beispiel     Alkali-n-          propylat    oder     n-propy        lalkoholischen    Alkalien,  umsetzt.  



  Das auf diese Weise gewonnene     a-n-Pro-          pyloxy-r-clrinolinearbonsäure-diäthylamid    bil  det farblose Kristalle vom Schmelzpunkt<B>611).</B>  Es ist in Mineralsäuren und in den meisten orga  nischen Lösungsmitteln ausserm kaltem     Petrol-          äther    leicht löslich.  



  Die neue Verbindung soll therapeutische  Verwendung finden.  



  <I>Beispiel:</I>  Eine     benzolische    Lösung von 2,2 Teilen     a-          Chlor#-r-chirrolincarbonsäurechlorid    wird unter  Kühlung allmählich mit<B>1,5</B> Teilen     Diäthyl-          amin    versetzt. Nach beendeter Reaktion wird  vom abgeschiedenen     Diäthylaminchlorhydrat          abfiltriert,    mit Benzol nachgewaschen und    das Lösungsmittel     abdestilliert.    Aus Alkohol  umkristallisiert bildet das     a-Chlor-r-chinolin-          car-bonsäure-diäthylamid    farblose Kristalle vom  Schmelzpunkt 124'.  



  10 Teile     a-Chlor-r-chirrolirrcarborrsäure-          diäthylamid    werden mit einer Lösung von  1 Teil     Natrium    in     n-Propylalkolrol    am     Rück-          Russ    gekocht. Nach beendeter Reaktion wird  der     n-Propylalkohol        abdestilliert    und der Rück  stand mit Äther und Wasser ausgeschüttelt.  Die ätherische Lösung hinterlässt beim Ver  dampfen ein fast farbloses Ö1, das allmählich  erstarrt.

   Das     a-rr-Pr,opyloxy-r-chinolirrcarborr-          säure-diäthylamid    lässt sich aus     Petroläther          umkristallisieren.     



  Statt mit     Natrium-n-propylat    kann die  Umsetzung auch mit andern alkalischen     Pro-          pylierungsmitteln,    wie zum Beispiel mit Als       kali    in wässerig     n-1>ropylalkoholischer    Lösung  erfolgen.



  Process for the preparation of a substituted quinoline carboxylic acid derivative. It has been found that a substituted quinolinecarboxylic acid derivative is obtained if diethylamine is allowed to act on the a-halo-r-chirrolircarboxylic acid halide and the a-halo-i-quinolinecarboric acid diethylamide obtained with alkaline propyling agents ,

      such as alkali n-propylate or n-propy lalcoholic alkalis, for example.



  The an-propyloxy-r-clrinolinearboxylic acid diethylamide obtained in this way forms colorless crystals with a melting point <B> 611). </B> It is easily soluble in mineral acids and in most organic solvents apart from cold petroleum ether .



  The new compound should find therapeutic use.



  <I> Example: </I> A benzene solution of 2.2 parts of a-chloro-r-chirroline carboxylic acid chloride is gradually admixed with 1.5 parts of diethylamine while cooling. When the reaction has ended, the precipitated diethylamine chlorohydrate is filtered off, washed with benzene and the solvent is distilled off. Recrystallized from alcohol, the a-chloro-r-quinoline-carboxylic acid diethylamide forms colorless crystals with a melting point of 124 '.



  10 parts of a-chloro-r-chirrolirrcarborric acid diethylamide are boiled on the back carbon black with a solution of 1 part of sodium in n-propyl alcohol. After the reaction has ended, the n-propyl alcohol is distilled off and the residue is extracted with ether and water. When evaporating, the ethereal solution leaves an almost colorless oil, which gradually solidifies.

   The a-rr-Pr, opyloxy-r-quinolirrcarborric acid diethylamide can be recrystallized from petroleum ether.



  Instead of using sodium n-propoxide, the reaction can also be carried out with other alkaline propylating agents, such as, for example, with Al-potassium in an aqueous n-propyl alcoholic solution.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines substi tuierten Chinolincarbor)säurederivates, dadurch gekennzeichnet, dass man auf a-Halogen-r- chinolincarborrsäurehalogenid Diäthylamirr ein wirken lässt und das erhaltene a-Halogerr-Y- chinolirrcarbonsätrre-diäthylamid mit alkali schen Propylierungsmitteln urnsetzt. Das auf diese Weise gewonnene a-n-Pro- pyloxy-r-chinolincarborrsäure-diäthylamid bil det farblose Kristalle vom Schmelzpunkt<B>610.</B> Es ist in 1Vlineralsäuren PATENT CLAIM: Process for the preparation of a substituted quinolinecarboric acid derivative, characterized in that diethylamine is allowed to act on a-halo-r-quinolinecarboric acid halide and the α-halogerr-Y-quinolirrcarboxylic acid derivative is reacted with alkaline propylating agents. The a-n-propyloxy-r-quinolinecarboric acid diethylamide obtained in this way forms colorless crystals with a melting point of <B> 610. </B> It is in mineral acids undin den meisten orga- nischen Lösungsmitteln ausser in kaltem Petroläther leicht löslich. Die neue Verbindung soll therapeutische Verwendung finden. and easily soluble in most organic solvents except in cold petroleum ether. The new compound should find therapeutic use.
CH125406D 1926-04-30 1926-04-30 Process for the preparation of a substituted quinoline carboxylic acid derivative. CH125406A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH125406T 1926-04-30
CH124228T 1929-04-17

Publications (1)

Publication Number Publication Date
CH125406A true CH125406A (en) 1928-04-16

Family

ID=25710213

Family Applications (1)

Application Number Title Priority Date Filing Date
CH125406D CH125406A (en) 1926-04-30 1926-04-30 Process for the preparation of a substituted quinoline carboxylic acid derivative.

Country Status (1)

Country Link
CH (1) CH125406A (en)

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