CH125399A - 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
CH125399A
CH125399A CH125399DA CH125399A CH 125399 A CH125399 A CH 125399A CH 125399D A CH125399D A CH 125399DA CH 125399 A CH125399 A CH 125399A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
preparation
acid derivative
quinoline
quinoline carboxylic
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 CH125399A publication Critical patent/CH125399A/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

Landscapes

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

Description

  

  erfahren zur Darstellung eines     substituierten        Chinollincarbonsäurederivates.       Es wurde gefunden, dass man zu einem  substituierten     Chinolincarbonsäurederivat    ge  langt, wenn man auf     a-Halogen-r-chinolin-          carbonsäure-halogenid        Diäthylamin    einwirken  lässt und das erhaltene     a-Halogen-9--chiriolin-          carbonsäure-diäthylamid    mit alkalischen     Äthy-          lierungsmitteln,    wie zum Beispiel     Alkaliäthylat     oder     äthylalkoliolischen    Alkalien, umsetzt.  



  Das auf diese Weise gewonnene     cc        Äthoxy-          r-chinolincarbonsäure-diäthylamid    bildet farb  lose Kristalle vom Schmelzpunkt 68  . Es  ist in Mineralsäuren und in den meisten or  ganischen     Lösungsmitteln    ausser in kaltem       Petroläther    leicht löslich.  



  Die neue Verbindung soll therapeutische  Verwendung finden.  



  <I>Beispiel:</I>  Eine     benzolische    Lösung von 2,2 Teilen       (x-Chlor-7--chinolincarbonsäurechlorid        wirdunter     Kühlung allmählich mit 1,5 Teilen     Diäthyl-          amin    versetzt. Nach beendeter Reaktion wird  vom abgeschiedenen     Diäthylaminchlorhydrat          abfiltriert,    mit Benzol nachgewaschen und    das Lösungsmittel     abdestilliert.    Aus     Alkoho:     umkristallisiert bildet das     a-Chlor-r-chiriolin          carbonsäure-diäthylamid    farblose Kristall(  vom Schmelzpunkt     1241'.     



  10,5 Teile     a-Chlor-r-chinolincarbonsäui#e          diäthylamid    werden mit einer Lösung 1     Tei     Natrium in     Äthylalkohol    am     Rückfluss        ge     kocht. Nach beendeter Reaktion wird de:  Alkohol     abdestilliert    und der Rückstand     mi     Äther und Wasser ausgeschüttelt.

   Die     äthe          rische    Lösung hinterlässt beim     Verdampfei     ein fast farbloses Öl, das allmählich erstarrt  Das     a-Äthogy-r-chinolincarbonsäure-diäthyl          amid    lässt sich aus     Petroläther        umkristalli          sieren.     



  Statt mit     Natriümäthylat    kann die Um  Setzung auch mit andern alkalischen     Äthy          lierungsmitteln,    wie zum Beispiel mit     Alkal     in wässerig alkoholischer Lösung erfolgen



  experience for the preparation of a substituted quinolline carboxylic acid derivative. It has been found that a substituted quinoline carboxylic acid derivative is obtained if diethylamine is allowed to act on a-halo-r-quinoline-carboxylic acid halide and the a-halo-9-chirioline-carboxylic acid diethylamide obtained is treated with alkaline ethylening agents , such as alkali ethylate or ethyl alcoholic alkalis.



  The cc ethoxy-r-quinolinecarboxylic acid diethylamide obtained in this way forms colorless crystals with a melting point of 68. It is easily soluble in mineral acids and in most organic solvents except in cold petroleum ether.



  The new compound should find therapeutic use.



  <I> Example: </I> A benzene solution of 2.2 parts of (x-chloro-7-quinoline carboxylic acid chloride is gradually added with 1.5 parts of diethylamine while cooling. After the reaction has ended, the separated diethylamine chlorohydrate is filtered off with benzene The a-chloro-r-chiriolin carboxylic acid diethylamide, when recrystallized from alcohol, forms colorless crystals (melting point 1241 '.



  10.5 parts of a-chloro-r-quinolincarbonsäui # e diethylamide are refluxed with a solution of 1 part of sodium in ethyl alcohol. After 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 on evaporation, which gradually solidifies. The a-ethogy-r-quinolinecarboxylic acid diethyl amide can be recrystallized from petroleum ether.



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

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines substi tuierten Chiriolincarbonsäurederivates, dadurcl gekennzeichnet, dass man auf a-Halogen-r chinoliiicarbonsäurehalogenid Diäthylamin ein wirken lässt und das erhaltene a-Halogen-r- chinolincarbonsäure-diäthylamid mit alkali schen Äthylierungsmitteln umsetzt. Das auf diese Weise gewonnene a-Äthoxy- r-chinolincarbonsäure-diäthylamid bildet farb lose Kristalle vom Schmelzpunkt 68 . PATENT CLAIM: Process for the preparation of a substituted chirioline carboxylic acid derivative, characterized by the fact that diethylamine is allowed to act on a-halo-r-quinoline-carboxylic acid halide and the α-halo-r-quinoline-carboxylic acid diethylamide is reacted with alkaline ethylating agents. The a-ethoxy-r-quinolinecarboxylic acid diethylamide obtained in this way forms colorless crystals with a melting point of 68. Es ist in Mineralsäuren und in den meisten organi schen Lösungsmitteln ausser in kaltem Petrol- äther 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.
CH125399D 1926-04-30 1926-04-30 Process for the preparation of a substituted quinoline carboxylic acid derivative. CH125399A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH125399T 1926-04-30
CH124228T 1929-04-17

Publications (1)

Publication Number Publication Date
CH125399A true CH125399A (en) 1928-04-16

Family

ID=25710206

Family Applications (1)

Application Number Title Priority Date Filing Date
CH125399D CH125399A (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) CH125399A (en)

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