CH144504A - Process for the preparation of a substituted quinoline carboxylic acid derivative. - Google Patents

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

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Publication number
CH144504A
CH144504A CH144504DA CH144504A CH 144504 A CH144504 A CH 144504A CH 144504D A CH144504D A CH 144504DA CH 144504 A CH144504 A CH 144504A
Authority
CH
Switzerland
Prior art keywords
preparation
acid derivative
quinolinecarboxylic acid
carboxylic acid
base
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 CH144504A publication Critical patent/CH144504A/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)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines     substituierten        Chinolinearbonsäurederivates.       Es wurde gefunden, dass man zu einem  substituierten     C'hinolincarbonsäurederivat    ge  langt, wenn man auf     a-Halogen-y-chinolin-          carbonsäurehalogenid    Anilin einwirken lässt  und das erhaltene     a-Halogen-y-chinolinear-          bonsäure-anilid    mit alkalischen Mitteln, die  zur Einführung der     Piperidinoäthoxygruppe     dienen, wie zum Beispiel     Piperidinoäthanol-          natrium    oder     Piperidinoäthanol    bei Gegen  wart von Alkali, umsetzt.

    



  Das auf diese Weise gewonnene     a-Piperi-          dinoätl-ioxy-y-chinolincarbonsä.ure-anilid    bil  det nahezu farblose Kristalle vom Schmelz  punkt 1<B>7</B>2  . Die Base ist in Wasser schwer,  in Benzol, Alkohol,     so-ivie    in warmem Essig  ester gut löslich. Die     einsäurigen    Salze der  Base lösen sich in Wasser mit neutraler  Reaktion.  



  Die neue Verbindung soll therapeutische  Verwendung finden.  



  <I>Beispiel:</I>  Eine     benzolische    Lösung von 22 Teilen       a-Chlor-y-chinolinearborlsäurechlorid    versetzt    man allmählich in Gegenwart einer wässe  rigen Lösung von 4 Teilen     Natriumhydroxyd     unter kräftigem Umrühren mit einer     benzo-          lischen    Lösung von 9,3 Teilen Anilin. Das  ausgefallene     a-Chlor-y-chinolincarbonsäure-          anilid    wird abgesaugt, gewaschen und ge  trocknet.

   Es schmilzt bei 202  . ,  Dann wird eine Lösung von 1,2 Teilen  Natrium in überschüssigem     Piperidinoätha-          nol    mit 14 Teilen     a-Chlor-y-chinolincarbon-          säure-anilid    bis zur Beendigung der Koch  salzabscheidung erwärmt. Das überschüssige       Piperidinoäthanol    wird zweckmässig im Va  kuum     abdestilliert    und der Rückstand in ver  dünnter Schwefelsäure aufgenommen. Ver  setzt man die Lösung mit. verdünnter Soda.  so fällt das     a-Piperidino-y-chinolincarbon-          säurea.nilid    in fester Form aus. Die Base  lässt sich aus Essigester     umkristallisieren.     



  Statt mit     Piperidinoäthanolnatrium    kann  die Umsetzung auch mit andern alkalischen  Mitteln, die zur Einführung der     Piperidino-          äthoxygruppe    dienen, wie zum Beispiel           Piperidinoäthanol    bei     Gegenwart    von Alkali  erfolgen.



  Process for the preparation of a substituted quinolinearboxylic acid derivative. It has been found that one reaches a substituted C'hinolincarbonsäurederivat ge, if one allows aniline to act on a-halo-y-quinoline-carboxylic acid halide and the resulting a-halo-y-quinolinear- anilide with alkaline agents, the Introduction of the piperidinoethoxy group, such as sodium piperidinoethanol or piperidinoethanol in the presence of alkali, is implemented.

    



  The α-piperidinoätl-ioxy-y-quinolinecarboxylic acid anilide obtained in this way forms almost colorless crystals with a melting point of 1 7 2. The base is difficult to dissolve in water and readily soluble in benzene, alcohol, and warm ethyl acetate. The mono-acidic salts of the base dissolve in water with a neutral reaction.



  The new compound should find therapeutic use.



  <I> Example: </I> A benzene solution of 22 parts of a-chloro-y-quinolinearboric acid chloride is gradually added in the presence of an aqueous solution of 4 parts of sodium hydroxide with vigorous stirring with a benzene solution of 9.3 parts of aniline . The precipitated α-chloro-γ-quinolincarboxylic acid anilide is filtered off with suction, washed and dried.

   It melts at 202. Then a solution of 1.2 parts of sodium in excess piperidinoethanol with 14 parts of α-chloro-γ-quinolinecarboxylic acid anilide is heated until the sodium chloride has separated out. The excess piperidinoethanol is expediently distilled off in vacuo and the residue is taken up in dilute sulfuric acid. You put the solution with. diluted soda. the a-piperidino-y-quinolincarboxylic acid a.nilide precipitates in solid form. The base can be recrystallized from ethyl acetate.



  Instead of sodium piperidinoethanol, the reaction can also be carried out with other alkaline agents which serve to introduce the piperidinoethoxy group, such as, for example, piperidinoethanol in the presence of alkali.

Claims (1)

PATENTANSPRUCH: Zerfahren zur Darstellung eines substi tuierten Chinolinearbonsäurederivates, da durch gekennzeichnet, dass man auf a-Halo- ben - y - chinolincarbonsäurehalogenid Anilin einwirken lässt und das erhaltene a-Haloben- y-chinolincarbonsäure-anilid mit alkalischen Mitteln, die zur<B>Ei</B> infürung der Piperidino- äthoxybruppe dienen, umsetzt. PATENT CLAIM: Process for the preparation of a substituted quinolinearboxylic acid derivative, characterized in that aniline is allowed to act on a-halobene - y - quinolinecarboxylic acid halide and the a-halobene-y-quinolinecarboxylic acid anilide with alkaline agents, which for <B> Egg </B> serving the piperidino ethoxy group, implemented. Das auf diese Weise gewonnene a-Piperi- dinoäthoxy-y-chinolincarbonsäure-anilid bil det nahezu farblose Kristalle vom Schmelz punkt<B>172</B> . Die Base ist in Wasser schwer, in Benzol, Alkohol, sowie in warmem Essig ester gut löslich. Die einsäurigen Salze der Base lösen sich in Wasser mit. neutraler Reaktion. Die neue Verbindung soll therapeutische Verwendung finden. The α-piperidinoethoxy-y-quinolinecarboxylic acid anilide obtained in this way forms almost colorless crystals with a melting point of <B> 172 </B>. The base is difficult in water and readily soluble in benzene, alcohol and warm ethyl acetate. The mono-acidic salts of the base dissolve in water. neutral reaction. The new compound should find therapeutic use.
CH144504D 1929-04-17 1929-04-17 Process for the preparation of a substituted quinoline carboxylic acid derivative. CH144504A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH124228T 1929-04-17
CH144504T 1929-04-17

Publications (1)

Publication Number Publication Date
CH144504A true CH144504A (en) 1930-12-31

Family

ID=25710217

Family Applications (1)

Application Number Title Priority Date Filing Date
CH144504D CH144504A (en) 1929-04-17 1929-04-17 Process for the preparation of a substituted quinoline carboxylic acid derivative.

Country Status (1)

Country Link
CH (1) CH144504A (en)

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