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CH125401A - 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
CH125401A
CH125401A CH125401DA CH125401A CH 125401 A CH125401 A CH 125401A CH 125401D A CH125401D A CH 125401DA CH 125401 A CH125401 A CH 125401A
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 CH125401A publication Critical patent/CH125401A/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

  

  
EMI0001.0001     
  
    Verfahren <SEP> zur <SEP> Darstellung <SEP> eines <SEP> substituierten <SEP> Chiaolincarbonsäurederivates.       Es wurde gefunden,     da1)    man zu einem  substituierten     Chinolincarbonsäurederivat    ge  langt, wenn man auf     ct-Halogen-r        -chirioliu-          carbonsäurehalogenid        Diallylamin    einwirken       iä        sst    und das erhaltene     a-Halogerl-r-chinolin-          carborisäul-e-diallylaiiiid    mit alkalischen     Äthy-          lierungsmitteln,

      wie zum Beispiel     Alkaliäthy-          lat    oder     äthylalkoliolischen    Alkalien, umsetzt.  



  Das auf diese Weise gewonnene a     .Ä-thoxy-          r-chinoliDcarbonsäure-diallylamid    bildet farb  lose Kristalle vom     Sinp.        53 .    Es ist in     3Iine-          ralsäuren        lind    in den meisten organischen  Lösungsmitteln ausser in kaltem     Petrolätlier     leicht löslich.  



  Die neue Verbindung soll therapeutische  Verwendung finden.  



  <I>Beispiel</I>  Eine     berizolische    Lösung von 1 Teil a  Cblor-r-chinoliucarbonsäurechlorid wird unter  Kühlung allmählich mit 0,9 Teilen     Diallylamin     versetzt. Nach beendeter Reaktion wird vom  abgeschiedenen     Diallylaminahlorhydrat        abfil-          triert,    mit Benzol nachgewaschen und das  Lösungsmittel     abdestilliert.    Aus Alkohol um-    kristallisiert bildet das     a-Chlor-r-chinolincai--          bonsäui-e-dial@lylamid    farblose Kristalle vom       Smp.    1U4 .  



  13 Teile     c-Clilor-r        -chirioliricarbonsäure-di-          allylamid    werden mit einer Lösung von 1 Teil  Natrium in     Äthylalkohol    am     Rückfluh    ge  kocht. Nach beendigter Reaktion wird der  Alkohol     abdestilliert    und der     Rückstand        "tont,     Äther und Wasser ausgeschüttelt.     Dic:,-:tC'ie-          zische        Lösung        hinterlässt    beim Verdampfen  ein fast farbloses Öl, das     allmählich    erstarrt.

    Das     a-Äthoxy-r-chiiiolincarboiisäui-e-diallyl-          amid    lässt sich aus     Petroläther        umki-i,".-lli-          sieren.     



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



  
EMI0001.0001
  
    Method <SEP> for <SEP> representation <SEP> of a <SEP> substituted <SEP> chiaolin carboxylic acid derivative. It has been found that a substituted quinoline carboxylic acid derivative is obtained if diallylamine is acted on ct-halo-r -chirioliucarboxylic acid halide and the a-halo-r-quinoline-carboric acid-e-diallylaiiiid is reacted with alkaline ethy- lubricants,

      such as alkali ethyl or ethyl alcoholic alkalis.



  The α-thoxy-r-quinoliDcarboxylic acid diallylamide obtained in this way forms colorless crystals of Sinp. 53. It is easily soluble in three-dimensional acids and in most organic solvents, except in cold petroleum ether.



  The new compound should find therapeutic use.



  <I> Example </I> 0.9 part of diallylamine is gradually added to a Berizolian solution of 1 part of a Cblor-r-quinoliucarboxylic acid chloride while cooling. After the reaction has ended, the diallylamine achlorohydrate which has separated out is filtered off, washed with benzene and the solvent is distilled off. Recrystallized from alcohol, the a-chloro-r-quinolincai-- bonsäui-e-dial @ lylamide forms colorless crystals with a melting point of 1U4.



  13 parts of c-Clilor-r-chirioliricarboxylic acid-dial allylamide are refluxed with a solution of 1 part of sodium in ethyl alcohol. When the reaction is complete, the alcohol is distilled off and the residue is tinted, ether and water are shaken out. The solution leaves an almost colorless oil on evaporation, which gradually solidifies.

    The a-ethoxy-r-chiiiolincarboiisäui-e-diallyl amide can be converted from petroleum ether.



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

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines substi tuierten Chinolincai-bonsäurederivates, dadurch gekennzeichnet, dass man auf a-Halogen-r- chinolincarbonsäurehalogenid Diallylamin ein wirken lässt und das erhaltene a-Halog;en-r- chinolincarbonsäure-diallylatnid mit alkali schen Äthylierungsmitteln umsetzt. Das auf diese Weise gewonnene, a-Äthoxy- Y-chiriolincarbonsäure-diallylamid bildet farb lose Kristalle vom Srnp. 53 . PATENT CLAIM: A process for the preparation of a substituted quinoline carboxylic acid derivative, characterized in that diallylamine is allowed to act on a-halo-r-quinoline carboxylic acid halide and the α-halo; en-r-quinoline carboxylic acid diallylate not obtained is reacted with alkaline ethylating agents. The a-ethoxy-Y-chirioline carboxylic acid diallylamide obtained in this way forms colorless crystals of the Srnp. 53. Es ist in Mine 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 mineral acids and in most organic solvents except in cold petroleum ether. The new compound should find therapeutic use.
CH125401D 1926-04-30 1926-04-30 Process for the preparation of a substituted quinoline carboxylic acid derivative. CH125401A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH125401T 1926-04-30
CH124228T 1929-04-17

Publications (1)

Publication Number Publication Date
CH125401A true CH125401A (en) 1928-04-16

Family

ID=25710208

Family Applications (1)

Application Number Title Priority Date Filing Date
CH125401D CH125401A (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) CH125401A (en)

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