CH125407A - 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
CH125407A
CH125407A CH125407DA CH125407A CH 125407 A CH125407 A CH 125407A CH 125407D A CH125407D A CH 125407DA CH 125407 A CH125407 A CH 125407A
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 CH125407A publication Critical patent/CH125407A/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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

  

  Verfahren zur Darstellung eines substituierten     Chinolincarbonsäurederivates.       Es wurde gefunden, dass man zu einem  substituierten     Chinolincarbonsäurederivat    ge  langt, wenn man auf     a-Halogen-r-chinolin-          carbonsäurehalogenid        Diäthylamin    einwirken  lässt und das erhaltene     a-Halogen-r-chinolin-          carbonsäure-diäthylamid    mit alkalischen Mit  teln, die zur Einführung der     Cyclohexyloxy-          gruppe    dienen,

   wie zum Beispiel     Cyclohexa-          nolnatrium    oder     Cyclohexanol    bei Gegenwart  von Alkali, umsetzt.  



  Das auf diese Weise gewonnene     a-Cyclo-          hexyloxy    -     r    -     chinolincarbonsäure    -     diätbylamid     bildet farblose Kristalle vom     Smp.    63 . Es  ist in Mineralsäuren und in den meisten or  ganischen Lösungsmitteln ausser in kaltem       Petroläther    leicht löslich.  



  Die neue Verbindung soll therapeutische  Verwendung finden.  



       Beispiel:     Eine     benzolische    Lösung von 2,2 Teilen  <I>a -</I> Chlor -     r   <I>-</I>     chinolincarbonsäurechlorid    wird  unter Kühlung allmählich mit 1,5 Teilen       Diäthylamin    versetzt. Nach beendeter Reak  tion wird vom abgeschiedenen Diäthylamin-         chlorhydrat        abfiltriert,    mit Benzol nachge  waschen und das Lösungsmittel     abdestilliert.     Aus Alkohol umkristallisiert bildet das a  Chlor-r-chinolincarbonsäure-diäthylamid farb  lose Kristalle vom     Smp.        1241-.     



  Hierauf werden 12 Teile     Cyclohexanol    in  70 Teilen     Xylol    mit 2,5 Teilen Natrium ge  kocht bis alles Natrium verschwunden ist.  Nach Zugabe von 26 Teilen     a-Chlor-r-chir)o-          lincarbonsäure-diäthylamid    -wird weiter ge  kocht, nach vollendeter Umsetzung mit Wasser  ausgeschüttelt und das Lösungsmittel     abde-          stilliert.    Das     ca-Cyclohexyloxy-Y-chinoliticar-          bonsäure-diäthylamid        hinterbleibt    als langsam  erstarrendes, nahezu farbloses Öl. Es lässt  sich aus     Petroläther        umkristallisieren.     



  Statt mit     Cyclohexanolnatrium    kann die  Umsetzung auch mit andern alkalischen Mit  teln, die zur Einführung der     Cyclohexyloxy-          gruppe    dienen, wie zum Beispiel     Cyclohexa-          nol    bei Gegenwart von Alkali 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-halo-r-quinoline-carboxylic acid halide and the a-halo-r-quinoline-carboxylic acid diethylamide obtained with alkaline means that introduce serve the cyclohexyloxy group,

   such as, for example, sodium cyclohexanol or cyclohexanol in the presence of alkali.



  The a-cyclohexyloxy - r - quinolinecarboxylic acid - dietbylamide obtained in this way forms colorless crystals with a melting point of 63. 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 <I> a - </I> chlorine - r <I> - </I> quinoline carboxylic acid chloride is gradually mixed with 1.5 parts of diethylamine while cooling. After 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-quinolinecarboxylic acid diethylamide forms colorless crystals with a melting point of 1241-.



  Then 12 parts of cyclohexanol in 70 parts of xylene are boiled with 2.5 parts of sodium until all of the sodium has disappeared. After adding 26 parts of a-chloro-r-chir) olincarboxylic acid diethylamide, the boiling is continued, shaken out with water when the reaction is complete and the solvent is distilled off. The ca-cyclohexyloxy-Y-quinoliticarboxylic acid diethylamide remains as a slowly solidifying, almost colorless oil. It can be recrystallized from petroleum ether.



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

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines substi tuierten Chinolincarbonsäurederivates, dadurch gekennzeichnet, dass man auf a-Halogen-Y- chinolincarbonsäurehalogenid Diäthylamin ein wirken lässt und das erhaltene a-Halogen-r- chinolincarbonsäure-diäthylainid mit alkali schen Mitteln, die zur Einführung der Cyclo- hexyloxygruppe dienen, umsetzt. PATENT CLAIM: Process for the preparation of a substituted quinoline carboxylic acid derivative, characterized in that diethylamine is allowed to act on a-halo-Y-quinoline carboxylic acid halide and the a-halo-r-quinoline carboxylic acid diethylainide obtained is treated with alkaline agents which are used to introduce the cyclo- hexyloxy group are used. Das auf diese Weise gewonnene a-Cyclo- hexyloxy -;r - chinolincarboneäure - diäthylamid bildet farblose Kristalle vom Smp. <B>63</B> . Es ist in Mineralsäuren und in den meisten or ganischen Lösungsmitteln ausser in kaltem Petroläther leicht löslich. Die neue Verbindung soll therapeutische Verwendung finden. The a-cyclohexyloxy -; r - quinolinecarbonic acid - diethylamide obtained in this way forms colorless crystals with a melting point of <B> 63 </B>. It is easily soluble in mineral acids and in most organic solvents except in cold petroleum ether. The new compound should find therapeutic use.
CH125407D 1926-04-30 1926-04-30 Process for the preparation of a substituted quinoline carboxylic acid derivative. CH125407A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH125407T 1926-04-30
CH124228T 1929-04-17

Publications (1)

Publication Number Publication Date
CH125407A true CH125407A (en) 1928-04-16

Family

ID=25710214

Family Applications (1)

Application Number Title Priority Date Filing Date
CH125407D CH125407A (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) CH125407A (en)

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