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CH125402A - 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
CH125402A
CH125402A CH125402DA CH125402A CH 125402 A CH125402 A CH 125402A CH 125402D A CH125402D A CH 125402DA CH 125402 A CH125402 A CH 125402A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
quinoline carboxylic
preparation
acid derivative
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 CH125402A publication Critical patent/CH125402A/en

Links

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

      Verfahren    zur Darstellung eines substituierten     Chinolinearbonsäurederivates.       Es wurde gefunden, dass     man    zu einem  substituierten     Chinolincarbonsäurederivat    ge  langt, wenn man auf     a-Halogen-r-chinolin-          carbonsäurelialogenid        Piperidin    einwirken lässt       und    das erhaltene     a-Halogen-r-chinoliiicarbon-          ":

  äru@e-piperidid    mit alkalischen     Äthylierungs-          initteln,    wie zum Beispiel     Alkaliäthylat    oder       äthylalkoholisehen        Alkalien,    umsetzt.  



  Das auf diese Weise     gewonnene        a-Äthoxy-          7--chinolincarbonsäure-piperidid    bildet farblose  Kristalle vom     Smp.    90 . Es ist in Mineral  säuren und in den meisten organischen Lö  sungsmitteln ausser in kaltem     Petroläther     leicht löslich.  



  Die neue     Verbindung    soll therapeutische  Verwendung finden.  



       Beispiel:     Eine     benzolische    Lösung von 9 Teilen       a-Chlor-r-chinolincai-bonsäurechlorid    wird unter  Kühlung allmählich mit 7 Teilen     Piperidin     versetzt. Nach beendeter Reaktion wird vom  abgeschiedenen     Piperidinchlorhydrat        abfiltriert,     mit Benzol nachgewaschen und das Lösungs  mittel     abdestilliert.    Aus Alkohol unikristalli-         siert    bildet das     a-Chlor-r-chinolincarbonsärn-e-          piperidid    farblose Kristalle vom     Smp.    140 .  



  11 Teile     a-Chlor-r-chinolincarbonsäure-          piperidid    werden mit einer Lösung von 1 Teil  Natrium in     Äthylalkohol    am     Rückfluss    ge  kocht. Nach beendeter Reaktion wird der  Alkohol     abdestilliert    und der Rückstand mit  Äther und Wasser ausgeschüttelt. Die äthe  rische Lösung hinterlässt beim Verdampfen  ein fast farbloses<B>01,</B> das allmählich erstarrt.  Das     a-Ätlioxy-r-chirioliricarborisäure-piperidid     lässt sich aus     Petroläther        umkristallisieren.     



  Statt mit     Natriumäthylat        kann    die Um  setzung auch mit andern alkalischen     Äthy-          lierungsmitteln,    wie zum Beispiel mit Alkali  in wässerig alkoholischer Lösung erfolgen.



      Process for the preparation of a substituted quinolinearboxylic acid derivative. It has been found that a substituted quinoline carboxylic acid derivative is obtained if piperidine is allowed to act on a-halo-r-quinoline-carboxylic acid halide and the obtained a-halo-r-quinoliiicarbon- ":

  äru @ e-piperidid with alkaline ethylating agents, such as alkali ethylate or ethyl alcoholic alkalis, is reacted.



  The a-ethoxy-7-quinolinecarboxylic acid piperidide obtained in this way forms colorless crystals with a melting point of 90. It is easily soluble in mineral acids and in most organic solvents with the exception of cold petroleum ether.



  The new compound should find therapeutic use.



       Example: 7 parts of piperidine are gradually added to a benzene solution of 9 parts of a-chloro-r-quinolincai-bonsäurechlorid while cooling. After the reaction has ended, the piperidine chlorohydrate which has separated out is filtered off, washed with benzene and the solvent is distilled off. Unicrystallized from alcohol, the a-chloro-r-quinolinecarboxylic acid epiperidide forms colorless crystals with a melting point of 140.



  11 parts of a-chloro-r-quinolincarboxylic acid piperidide 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. When it evaporates, the ethereal solution leaves an almost colorless <B> 01 </B> that gradually solidifies. The a-Ätlioxy-r-chirioliricarborisäure-piperidid can be recrystallized from petroleum ether.



  Instead of sodium ethylate, the reaction can also be carried out with other alkaline ethylating agents, such as, for example, with alkali in an aqueous alcoholic solution.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines substi tuierten Chinolincarbonsäurederivates, dadurch gekennzeichnet, dass man auf a-Halogen-Y- chinolincarbonsärirehalogenid Piperidin ein wirken lässt und das erhaltene a-Halogeri-7-- chinolincarbonsäure-piperidid mit alkalischen Äthylierungsmitteln umsetzt. Das auf diese Weise gewonnene a-Äthoxy- Y-chinolincarbonsäure-piperidid bildet farblose Kristalle vom Smp. 90 . PATENT CLAIM: Process for the preparation of a substituted quinoline carboxylic acid derivative, characterized in that piperidine is allowed to act on a-halo-Y-quinoline carboxylic acid halide and the a-halo-7-quinoline carboxylic acid piperidide obtained is reacted with alkaline ethylating agents. The a-ethoxy-Y-quinolinecarboxylic acid piperidide obtained in this way forms colorless crystals with a melting point of 90. Es ist in Mineral säuren und in .den meisten organischen Lö- sungsmitteln ausser in kaltem Petroläther leicht löslich. Die neue Verbindung soll therapeLitische- Verwendung finden. It is easily soluble in mineral acids and in most organic solvents except in cold petroleum ether. The new connection should find therapeutic use.
CH125402D 1926-04-30 1926-04-30 Process for the preparation of a substituted quinoline carboxylic acid derivative. CH125402A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH125402T 1926-04-30
CH124228T 1929-04-17

Publications (1)

Publication Number Publication Date
CH125402A true CH125402A (en) 1928-04-16

Family

ID=25710209

Family Applications (1)

Application Number Title Priority Date Filing Date
CH125402D CH125402A (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) CH125402A (en)

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