CH125400A - 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
CH125400A
CH125400A CH125400DA CH125400A CH 125400 A CH125400 A CH 125400A CH 125400D A CH125400D A CH 125400DA CH 125400 A CH125400 A CH 125400A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
quinoline carboxylic
preparation
acid derivative
dipropylamide
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 CH125400A publication Critical patent/CH125400A/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     substituierten        Chinolincarbonsäurederivates.       Es wurde gefunden, dass man zu einem  substituierten     Chinolincarbonsäurederivat    ge  langt, wenn man auf     ts-Halogen-r-chi.nolin-          cai-borisäurehalogenid        Dipropylamin    einwirken  lässt und das erhaltene     a-Halogen-r-chinolin-          earbonsäure-dipropylamid    mit alkalischen       Äthyliei-ungsmitteln.    wie zum Beispiel Al  kaliäthylat oder     äthylalkoholischen    Alkalien,  umsetzt.  



  Das auf diese Weise gewonnene     a-Äthogy-          y-cliinoliriear#bonsäur#e-dipropylam.id    bildet farb  lose Kristalle vom     Smp.    60 . Es ist in     Mine-          ralsäuren    und in den meisten organischen  Lösungsmitteln ausser in kaltem     Petroläther     leicht löslich.  



  Die neue Verbindung soll therapeutische  Verwendung finden.  



       Beispiel:     Eine     benzolische    Lösung von 1 Teil     a-          Chlor-r        -ebinolincarbonsäui#eehlorid    wird unter  Kühlung allmählich mit 0,9 Teilen     Dipro-          pylamin    versetzt.

   Nach beendeter Reaktion  wird vom abgeschiedenen     Dipropylaminchlor-          hy        drat        abfiltriert,    mit Benzol nachgewaschen    und das Lösungsmittel     abdestilliert..    Aus       Petroläther    umkristallisiert bildet das     a-Chlor-          r-chinotiriöarboiisäure-dipropylamid    farblose  Kristalle vom     Smp.        77 .      12 Teile     a-Chlor-r-chinolincarbonsäure-          dipropylamid    werden mit einer Lösung von  1 Teil Natrium in     Äthylalkohol    am Rück  fluss gekocht.

   Nach beendeter Reaktion wird  der Alkohol     abdestilliert    und der Rückstand  mit Äther und Wasser ausgeschüttelt. Die  ätherische Lösung hinterlässt beim Verdamp  fen ein fast farbloses 01, das allmählich er  starrt. Das     a-Ätboxy-r-chinolincarbonsäure-          dipropylamid    lässt sich aus     Petroläther    um  kristallisieren,  Statt mit     Natriumäthylat    kann die Um  setzung auch mit andern alkalischen     Äthylie-          rungsmitteln,    wie zum Beispiel mit Alkali  in wässerig alkoholischer Lösung erfolgen.



  process for the preparation of a substituted quinoline carboxylic acid derivative. It has been found that a substituted quinoline carboxylic acid derivative is obtained if dipropylamine is allowed to act on ts-halo-r-chi.nolin- cai-boric acid halide and the a-halo-r-quinoline-carboxylic acid-dipropylamide is reacted with alkaline ethylie- resources. such as Al kaliäthylat or ethyl alcoholic alkalis, implemented.



  The a-ethogy-y-cliinoliriear # bonsäur # e-dipropylamide obtained in this way forms colorless crystals with a melting point of 60. It is easily soluble in mineral acids and in most organic solvents except in cold petroleum ether.



  The new compound should find therapeutic use.



       Example: 0.9 part of dipropylamine is gradually added to a benzene solution of 1 part of a-chloro-r-binoline carboxylic acid chloride, while cooling.

   After the reaction has ended, the dipropylamine chlorohydrate which has separated out is filtered off, washed with benzene and the solvent is distilled off. Recrystallized from petroleum ether, the α-chloro-r-quinotiriöarboiisäure-dipropylamide forms colorless crystals with a melting point of 77. 12 parts of a-chloro-r-quinolincarboxylic acid dipropylamide are refluxed with a solution of 1 part of sodium in ethyl alcohol.

   When the reaction has ended, the alcohol is distilled off and the residue is extracted by shaking with ether and water. The ethereal solution leaves behind an almost colorless oil when it evaporates, which gradually becomes staring. The a-Ätboxy-r-quinolincarboxylic acid dipropylamide can be recrystallized from petroleum ether. Instead of using sodium ethylate, it can also be reacted with other alkaline ethyla- ting agents, such as alkali in an aqueous alcoholic solution.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines substi tuierten Chinolincarbonsäurederivates, dadurch gekennzeichnet, dass man auf a-Halogen-r- chinolincarbonsäurehalogenid Dipropylamin einwirken lässt und das erhaltene a-Halogen- 7,-chinoliricarbonsäure-dipropylamid mit alka lischen Äthylierungsmitteln umsetzt. Das auf diese Weise gewonnene a-Äthoxy- r-chinolincarbonsäure-dipropylamid bildet farb lose Kristalle vom Smp. 60 . PATENT CLAIM: A process for the preparation of a substituted quinoline carboxylic acid derivative, characterized in that dipropylamine is allowed to act on a-halo-r-quinoline carboxylic acid halide and the α-halo-7, -quinoliricarboxylic acid-dipropylamide obtained is reacted with alkali ethylating agents. The a-ethoxy-r-quinolinecarboxylic acid-dipropylamide obtained in this way forms colorless crystals with a melting point of 60. Es ist in 1VIine- ralsäuren und in den meisten organischen Lösungsmitteln ausser in kaltem Petroläther leicht löslich. Die neue Verbindung soll therapeutische Verwendung finden. It is easily soluble in linear acids and in most organic solvents except in cold petroleum ether. The new compound should find therapeutic use.
CH125400D 1926-04-30 1926-04-30 Process for the preparation of a substituted quinoline carboxylic acid derivative. CH125400A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH125400T 1926-04-30
CH124228T 1929-04-17

Publications (1)

Publication Number Publication Date
CH125400A true CH125400A (en) 1928-04-16

Family

ID=25710207

Family Applications (1)

Application Number Title Priority Date Filing Date
CH125400D CH125400A (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) CH125400A (en)

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