CH125404A - 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
CH125404A
CH125404A CH125404DA CH125404A CH 125404 A CH125404 A CH 125404A CH 125404D A CH125404D A CH 125404DA CH 125404 A CH125404 A CH 125404A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
preparation
acid derivative
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 CH125404A publication Critical patent/CH125404A/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     Uhinolincarbonsäurederivates.       Es wurde gefunden, dass man zu einem       substituierten        Chinolincarbonsäurederivat    ge  langt, wenn man auf     a-Halogen-r-chinoliii-          carbonsäurehalogenid        Benzylamin    einwirken  lässt und das erhaltene     a-Halogen-r-chinolin-          tarbonsäure-benzylamid    mit alkalischen     Äthy-          lierungsmitteln,    wie z. B.     Alkaliäthylat    oder       äthylalkoholischen    Alkalien, umsetzt.  



  Das auf diese Weise erhaltene     a-Äthoxy-          r-chinolinoarbonsäure-benzylamid    bildet farb  lose Kristalle vom     Smp.   <B>1660.</B> Es ist in  Mineralsäuren löslich und lässt sich aus Alko  hol     umkristallisieren.     



  Die neue Verbindung soll therapeutische  Verwendung finden.  



  <I>Beispiel:</I>  Eine     berizolische    Lösung von 1 Teil     a-Chlor-          r-chinolincarbonsäureehlorid    wird unter Küh  lung allmählich mit 1 Teil     Benzylamin    ver  setzt. Nach beendeter Reaktion wird das  Benzol abgesaugt und der Rückstand mit    Wasser und Alkohol gewaschen. Aus Alko  hol umkristallisiert bildet das     a-Chlor-r-chino-          lincarbonsäure-benzylamid    farblose Kristalle  vom     Smp.    217  .  



  10 Teile     a-Chloi--r-chinolincarbonsäure-ben-          zylamid    werden mit einer Lösung von 1 Teil  Natrium in     Äthylalkohol    am     Rückfluss    ge  kocht. Nach beendeter Reaktion wird mit  Wasser versetzt. Das     a-Äthoxy-r-chinolin-          carbonsäure-ben7,ylamid    scheidet sich aus und  wird aus Alkohol umkristallisiert.  



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



  Process for the preparation of a substituted uhinoline carboxylic acid derivative. It has been found that a substituted quinoline carboxylic acid derivative is obtained if benzylamine is allowed to act on a-halo-r-quinoliii- carboxylic acid halide and the a-halo-r-quinoline-tarboxylic acid benzylamide obtained is reacted with alkaline ethy- ling agents, such as . B. alkali ethylate or ethyl alcoholic alkalis.



  The a-ethoxy-r-quinolinoarboxylic acid benzylamide obtained in this way forms colorless crystals with a melting point of <B> 1660. </B> It is soluble in mineral acids and can be recrystallized from alcohol.



  The new compound should find therapeutic use.



  <I> Example: </I> A Berizolian solution of 1 part of a-chloro-r-quinoline carboxylic acid chloride is gradually mixed with 1 part of benzylamine while cooling. After the reaction has ended, the benzene is filtered off with suction and the residue is washed with water and alcohol. Recrystallized from alcohol, the a-chloro-r-quinolinecarboxylic acid benzylamide forms colorless crystals with a melting point of 217.



  10 parts of a-Chloi - r-quinolincarboxylic acid benzylamide are refluxed with a solution of 1 part of sodium in ethyl alcohol. After the reaction has ended, water is added. The a-ethoxy-r-quinoline-carboxylic acid-ben7, ylamid separates and is recrystallized from alcohol.



  Instead of using sodium ethylate, the conversion can also be carried out with other alkaline ethy- ling agents, such as. B. be done with 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 Benzylamin ein wirken lässt und das erhaltene a-Halogen-r- chinolincarbonsäurebenzylacnid mit alkalischen Äthylierungsmitteln umsetzt. Das auf diese Weise gewonnene a-Äthogy- r-chinolincarbonsäure-benzylamid bildet farb lose Kristalle vom Smp. 166 . PATENT CLAIM: Process for the preparation of a substituted quinoline carboxylic acid derivative, characterized in that benzylamine is allowed to act on α-halo-r-quinolinecarboxylic acid halide and the α-halo-r-quinolinecarboxylic acid benzylacnide is reacted with alkaline ethylating agents. The a-ethogyr-quinolinecarboxylic acid benzylamide obtained in this way forms colorless crystals with a melting point of 166. Es ist in Mineralsäuren löslich und lässt sich aus Alko hol umkristallisieren. Die neue Verbindung soll therapeutische Verwendung finden. It is soluble in mineral acids and can be recrystallized from alcohol. The new compound should find therapeutic use.
CH125404D 1926-04-30 1926-04-30 Process for the preparation of a substituted quinoline carboxylic acid derivative. CH125404A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH125404T 1926-04-30
CH124228T 1929-04-17

Publications (1)

Publication Number Publication Date
CH125404A true CH125404A (en) 1928-04-16

Family

ID=25710211

Family Applications (1)

Application Number Title Priority Date Filing Date
CH125404D CH125404A (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) CH125404A (en)

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