CH125405A - 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
CH125405A
CH125405A CH125405DA CH125405A CH 125405 A CH125405 A CH 125405A CH 125405D A CH125405D A CH 125405DA CH 125405 A CH125405 A CH 125405A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
preparation
acid derivative
quinoline carboxylic
quinolinecarboxylic acid
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 CH125405A publication Critical patent/CH125405A/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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines substituierten     Chinolincarbonsäurederivates.       Es wurde gefunden, dass man zu einem  substituierten     Chinolincarbonsäärederivat    ge  langt, wenn man auf     a-Halogeri-y-chinoliir          carbonsäurehalogenid        Diäthylamin    einwirken  lässt und das erhaltene     a-Halogen-r-chinolin-          carbonsäurediät.hylamid    mit alkalischen     Methy-          lierungsmitteln,    wie z. B.     Alkalimethylat    oder       inethylalkoholischen    Alkalien umsetzt.  



  Das auf diese Weise gewonnene     a-Methoxy-          r        -chinoliricarbonsäure-diäthylamid    bildet farb  lose Kristalle vom Schmelzpunkt 93  . Es ist in  Mineralsäuren und in den meisten organischen  Lösungsmitteln ausser in kaltem     Petroläther     leicht löslich.  



  Die neue Verbindung soll therapeutische  Verwendung finden.  



       Beispiel:     Eine     benzolische    Lösung von 2,2 Teilen       cc-Chlor-r-chiriolincarbonsäurechloridwird    unter  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 Alkohol    umkristallisiert bildet das     a-Chlor-r-chiriolin-          carbonsäure-diäthylamid    farblose Kristalle vom  Schmelzpunkt 124 .  



  10 Teile     a-Chlor-r-chinolincarborisäure-          diäthylamid        ',werden    mit einer Lösung von  1 Teil Natrium in Methylalkohol am Rück  fluss gekocht. Nach beendeter Reaktion wird  der     Methylalkohol        abdestilliert    und der Rück  stand mit Äther und Wasser ausgeschüttelt.  Die ätherische Lösung hinterlässt beim Ver  dampfen ein fast farbloses Öl, das allmäh  lich erstarrt. Das     a-Methoxy-r-chinolincarbori-          säure-diäthylamid    lässt sich aus     Petroläther          umkristallisieren.     



  Statt mit     Natriummethylat    kann die Um  setzung auch mit andern alkalischen     Methy-          lierungsmitteln,    wie z. B. mit Alkali in wässerig       methylalkoholischer    Lösung erfolgen.



  Process for the preparation of a substituted quinoline carboxylic acid derivative. It has been found that a substituted quinoline carboxylic acid derivative is obtained if diethylamine is allowed to act on a-Halogeri-y-quinoliir carboxylic acid halide and the obtained a-halo-r-quinoline carboxylic acid diethylamide is reacted with alkaline methylating agents, such as. B. alkali metal or inethyl alcoholic alkalis.



  The a-methoxy-r-quinoliricarboxylic acid diethylamide obtained in this way forms colorless crystals with a melting point of 93. It is easily soluble in mineral acids and in most organic solvents except in cold petroleum ether.



  The new compound should find therapeutic use.



       Example: A benzene solution of 2.2 parts of cc-chloro-r-chirioline carboxylic acid chloride is gradually mixed with 1.5 parts of diethylamine while cooling. When the reaction has ended, the precipitated diethylamine chlorohydrate is filtered off, washed with benzene and the solvent is distilled off. Recrystallized from alcohol, the a-chloro-r-chiriolin-carboxylic acid diethylamide forms colorless crystals with a melting point of 124.



  10 parts of a-chloro-r-quinolincarboric acid diethylamide 'are refluxed with a solution of 1 part of sodium in methyl alcohol. After the reaction has ended, the methyl alcohol is distilled off and the residue is extracted with ether and water. When evaporating, the ethereal solution leaves an almost colorless oil that gradually solidifies. The a-methoxy-r-quinolinecarboric acid diethylamide can be recrystallized from petroleum ether.



  Instead of sodium methylate, the conversion can also be carried out with other alkaline methylating agents, such as. B. be done with alkali in aqueous methyl alcoholic solution.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines substi tuierten Chinolincarbonsäurederivates, dadurch gekennzeichnet, dass man auf a-Halogen-r- chinolincai-bonsäurehalogenid Diäthylamin ein wirken läl@t und das erhaltene a-Halogen-r- chinolincarborrsäure-diäthylarnid mit alkali- sehen lfethylierungsmitteln umsetzt. Das auf diese Weise gewonnene a-Methoay- r-chinolincarbonsäure-diätlryiaririd bildet farb lose Kristalle vom Schmelzpunkt 93 . PATENT CLAIM: Process for the preparation of a substituted quinolinecarboxylic acid derivative, characterized in that diethylamine is allowed to act on a-halo-r-quinolinecarboxylic acid halide and the a-halo-r-quinolinecarboric acid diethyl amide is reacted with alkali-see lfethylating agents. The a-methoayr-quinolinecarboxylic acid dietary arylide obtained in this way forms colorless crystals with a melting point of 93. Es ist in Mineralsäuren 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.
CH125405D 1926-04-30 1926-04-30 Process for the preparation of a substituted quinoline carboxylic acid derivative. CH125405A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH125405T 1926-04-30
CH124228T 1929-04-17

Publications (1)

Publication Number Publication Date
CH125405A true CH125405A (en) 1928-04-16

Family

ID=25710212

Family Applications (1)

Application Number Title Priority Date Filing Date
CH125405D CH125405A (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) CH125405A (en)

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