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CH139430A - Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. - Google Patents

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

Info

Publication number
CH139430A
CH139430A CH139430DA CH139430A CH 139430 A CH139430 A CH 139430A CH 139430D A CH139430D A CH 139430DA CH 139430 A CH139430 A CH 139430A
Authority
CH
Switzerland
Prior art keywords
acid
preparation
carboxylic acid
basic derivative
soluble
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 CH139430A publication Critical patent/CH139430A/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     basischen    Derivates einer     substituierten          Chinolinear    Bonsäure.    Es wurde gefunden,     da,B    man zu  einem basiseben Derivat einer substituierten       Chinolinca.rbonsäure        gelangt,

      wenn man auf       Säurehalogenide    der     2-Halogen-4-chinolincar-          bo-nsäure    asymmetrisches     Diäthyläthylendia-          min    einwirken lässt und das erhaltene     2-          Halogen    - 4-     chinolincarbonsäure    -     diäthyläthy-          lendiamid    mit alkalischen Mitteln, die zur  Einführung der     Benzyloxygruppe    dienen,  umsetzt.  



  Das     2-Benzyloxy-4-chinolincarbonsäure-          diäthyläthylendiamid    bildet farblose Kri  stalle vom Schmelzpunkt<B>119'.</B> Die Base ist  in kaltem     Petroläther    schwer löslich; in den  meisten organischen     Lösungsmitteln    ist     sie     besonders in der Wärme     gut    löslich. Mit  Säuren gibt sie neutrale, in Wasser leicht  lösliche Salze.  



  Die neue Verbindung soll zu therapeuti  schen Zwecken Verwendung finden.  <I>Beispiel:</I>  Zu einer Lösung von 1,2 Teilen asymme  trischem     Diäthyläthylendiamin    in 45 Teilen         10%        iger    Natronlauge gibt man unter Küh  lung und ständigem Umrühren allmählich  eine     benzolische    Lösung von 2,2 Teilen     2-          Chlor-4-chinolincarbonsäurechlorid    zu. Nach  .beendigter Reaktion wird die     benzolische    Lö  sung abgetrennt, die gebildete Base mit Salz  säure ausgezogen und mit Soda wieder aus  gefällt. Man nimmt die Base in Äther auf,  vertreibt das Lösungsmittel und kristallisiert  sie aus     Petroläther    um.

   Dass     2-CUor-4-chinolin-          carbonsäure-diäthyläthylendiamid    bildet farb  lose, blättrige Kristalle vom Schmelzpunkt  74'. In den meisten organischen Lösungs  mitteln ist die Base leicht löslich; mit Säu  ren bildet sie neutrale, wasserlösliche Salze.  



  2,5 Teile Natrium werden mit 13 Teilen       Benzylalkohol    durch Erwärmen in     Toluollö-          sung    umgesetzt. Hierauf gibt man 30 Teile  2 -     Chlor-4        -.chinolincarbonsäure        -.diäthyläthy-          lendiamid    hinzu und erwärmt im Ölbad bis  zur Beendigung der Reaktion. Man wäscht  mit Wasser aus und destilliert das Lösungs  mittel im Vakuum ab.

   Man erhält das 2-           Benzyloxy    - 4     -@chinolincarbonsäure    -     diäthyl-          äthvlendiamid    nach dem     Umkristallisieren     aus     Petroläther,    zweckmässig in Gegenwart  von etwas Benzol, in farblosen Kristallen.  



  Zur Einführung :der     Benzyloxygruppe     können auch andere     Metallbenzylate    in or  ganischen Lösungsmitteln oder zum Beispiel  auch Alkalien in Gegenwart von     Benzylalko-          hol    Verwendung finden.



  Process for the preparation of a basic derivative of a substituted quinolinear bonic acid. It was found that, B one arrives at a basic derivative of a substituted quinoline carboxylic acid,

      when asymmetric diethylethylenediamine is allowed to act on acid halides of 2-halo-4-quinolinecarboxylic acid and the 2-halo-4-quinolinecarboxylic acid obtained is reacted with alkaline agents which serve to introduce the benzyloxy group.



  The 2-benzyloxy-4-quinolinecarboxylic acid diethylethylenediamide forms colorless crystals with a melting point of <B> 119 '. </B> The base is sparingly soluble in cold petroleum ether; in most organic solvents it is readily soluble, especially when heated. With acids it gives neutral, easily soluble salts in water.



  The new connection is intended to be used for therapeutic purposes. <I> Example: </I> To a solution of 1.2 parts of asymmetric diethylethylenediamine in 45 parts of 10% sodium hydroxide solution, a benzene solution of 2.2 parts of 2-chloro-4- is gradually added with cooling and constant stirring quinoline carboxylic acid chloride too. After the reaction has ended, the benzene solution is separated off, the base formed is extracted with hydrochloric acid and precipitated out again with soda. The base is taken up in ether, the solvent is driven off and it is recrystallized from petroleum ether.

   That 2-CUor-4-quinolinecarboxylic acid diethylethylenediamide forms colorless, leafy crystals with a melting point of 74 '. The base is easily soluble in most organic solvents; with acids it forms neutral, water-soluble salts.



  2.5 parts of sodium are reacted with 13 parts of benzyl alcohol by heating in toluene solution. 30 parts of 2-chloro-4-quinoline-carboxylic acid -.diäthyläthylenediamid are then added and the mixture is heated in an oil bath until the reaction has ended. It is washed with water and the solvent is distilled off in vacuo.

   The 2-benzyloxy-4-@ quinolincarboxylic acid diethyl ether diamide is obtained in colorless crystals after recrystallization from petroleum ether, expediently in the presence of a little benzene.



  As an introduction: the benzyloxy group can also be used with other metal benzylates in organic solvents or, for example, alkalis in the presence of benzyl alcohol.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolincarbon- säure, dadurch gekennzeichnet, dass man auf Säurehalogenide der 2-Ha.logen-4-chinolincar- bonsäure asymmetrisches Diäthyläthylendia: min einwirken lässt und das erhaltene 2-Ha.- logen - 4 -chinalinc arbonäure- diäthytäthylen- diamid mit alkalischen Mitteln, die zur Ein führung der Benzyloxygruppe : PATENT CLAIM: Process for the preparation of a basic derivative of a substituted quinolinecarboxylic acid, characterized in that asymmetric diethylethylenedia: min is allowed to act on acid halides of 2-Ha.logen-4-quinolinecarboxylic acid and the resulting 2-Ha.- logen -4 -chinalinc carbonic acid diethytethylene diamide with alkaline agents that introduce the benzyloxy group: dienen, um setzt. Das 2 - Benzy loxy - 4 - chinolincarbon- säure-diäthyläthylendiamid bildet farblose Kristalle vom Schmelzpunkt 119 . Die Base ist in kaltem Petroläther schwer löslich; in den meisten organischen Lösungsmitteln ist besonders in der Wärme gut lös lich. Mit Säuren gibt sie neutrale, in Wasser leicht lösliohe Salze. Die neue Verbindung soll zu therapeuti schen Zwecken Verwendung finden. serve to sets. The 2 - benzy loxy - 4 - quinolincarboxylic acid diethylethylenediamide forms colorless crystals with a melting point of 119. The base is sparingly soluble in cold petroleum ether; in most organic solvents is particularly well soluble in heat. With acids it gives neutral salts which are easily soluble in water. The new connection is intended to be used for therapeutic purposes.
CH139430D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139430A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139430T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139430A true CH139430A (en) 1930-04-15

Family

ID=25712940

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139430D CH139430A (en) 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid.

Country Status (1)

Country Link
CH (1) CH139430A (en)

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