CH157848A - 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.

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Publication number
CH157848A
CH157848A CH157848DA CH157848A CH 157848 A CH157848 A CH 157848A CH 157848D A CH157848D A CH 157848DA CH 157848 A CH157848 A CH 157848A
Authority
CH
Switzerland
Prior art keywords
acid
preparation
carboxylic acid
petroleum ether
basic derivative
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 CH157848A publication Critical patent/CH157848A/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)
  • Plural Heterocyclic Compounds (AREA)

Description

  

      Verfahren    zur Darstellung eines basischen Derivates einer     substituierten          Chinolinearbonsäure.       Es wurde gefunden, dass man zu einem  basischen Derivat einer substituierten     Chino-          lincarbonsäure    gelangt,

       wenn    man auf Säure  halogenide der 2-     Halogen-4-chinolincarbon-          säure    asymmetrisches     Diäthyläthylendiamin     einwirken lässt und das erhaltene     2-Halogen-          4    -     chinolincarbonsäure    -     diäthyläthylendiamid     mit alkalischen Mitteln, die zur Einführung  der     Hexyloxygruppe    dienen, umsetzt.  



  Das     2-n-Hexyloxy-4-chinolincarbonsäure-          diätbyläthylendiamid    bildet farblose Kristalle  vom Schmelzpunkt 73 0. Die Base ist in kal  tem     Petroläther    schwer löslich; in warmem       Petroläther,    wie in den übrigen organischen  Lösungsmitteln ist sie leicht 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 Rühren allmählich eine       benzolische    Lösung von 2,2 Teilen     2-Chlor-          4-chinolincarbonsäurechlorid    zu.

   Nach been  deter Reaktion wird die     benzolische    Lösung  abgetrennt, die gebildete Base mit Salzsäure  ausgezogen und mit Soda wieder ausgefällt.  Man nimmt die Base in Äther auf, vertreibt  das Lösungsmittel und kristallisiert sie aus       Petroläther    um. Das     2-Chlor-4-chinolincarbon-          säure-diäthyläthylendiamid    bildet farblose,  blättrige Kristalle vom Schmelzpunkt 74'.  In den meisten organischen Lösungsmitteln  ist die Base leicht     lösli(;h;    mit Säuren bildet  sie neutrale, wasserlösliche Salze.  



  15 Teile     2-Chlor-4-chinolincarbonsäure-          diäthyläthylendiamid    werden mit einer Lösung  von 1,3 Teilen Natrium in     Hexylalkohol    ge  kocht. Hierauf wird der     ri-Hexylalkohol    ab  destilliert, der Rückstand in Äther aufge  nommen und mit Wasser gewaschen. Nach  Entfernung des Lösungsmittels verbleibt das  2 - n -     Hexyloxy-4-chinolincarbo        nsäure    - diäthyl-           äthylendiamid    als Öl, das alsbald zu farb  losen Kristallen erstarrt. Die Base lässt sich  aus     Petroläther        umkristallisieren.     



  An Stelle einer Lösung von     Alkalimetall     in     Hexylalkohol    können auch andere Mittel,  die zur Einführung der     Hexyioxygruppe    die  nen, Verwendung finden, zum Beispiel Alkali  hydroxyd in     Hegylalkohol.  



      Process for the preparation of a basic derivative of a substituted quinolinearboxylic acid. It has been found that a basic derivative of a substituted quinoline carboxylic acid is obtained,

       if you can act on acid halides of 2-halo-4-quinolincarboxylic acid asymmetric diethylethylenediamine and the 2-halo-4-quinolinecarboxylic acid - diethylethylenediamide with alkaline agents that serve to introduce the hexyloxy group, is implemented.



  The 2-n-hexyloxy-4-quinolincarboxylic acid dietbylethylenediamide forms colorless crystals with a melting point of 73 0. The base is sparingly soluble in cold petroleum ether; It is easily soluble in warm petroleum ether, as in the other organic solvents. 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 while cooling and with constant stirring -quinoline carboxylic acid chloride too.

   After the end of the reaction, the benzene solution is separated off, the base formed is extracted with hydrochloric acid and reprecipitated with soda. The base is taken up in ether, the solvent is driven off and it is recrystallized from petroleum ether. The 2-chloro-4-quinolinecarboxylic acid diethylethylenediamide forms colorless, leafy crystals with a melting point of 74 '. The base is easily soluble in most organic solvents (; h; with acids it forms neutral, water-soluble salts.



  15 parts of 2-chloro-4-quinolincarboxylic acid diethylethylenediamide are boiled with a solution of 1.3 parts of sodium in hexyl alcohol. Then the ri-hexyl alcohol is distilled off, the residue taken up in ether and washed with water. After removal of the solvent, the 2 - n - hexyloxy-4-quinolincarbo nic acid diethyl ethylenediamide remains as an oil, which soon solidifies to form colorless crystals. The base can be recrystallized from petroleum ether.



  Instead of a solution of alkali metal in hexyl alcohol, it is also possible to use other agents which serve to introduce the hexyioxy group, for example alkali hydroxide in hegyl alcohol.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolincarbon- säure, dadurch gekennzeichnet, dass man auf Säurehalogenide der 2-Halogen-4-chinolincar- bonsäure asymmetrisches Diäthyläthylendi- amin einwirken lässt und das erhaltene 2- Halogen-4-chir#olincarbonsäure-diäthyläthylen- diamid mit alkalischen Mitteln, die zur Ein führung der Hexyloxygruppe dienen, umsetzt. Claim: Process for the preparation of a basic derivative of a substituted quinolinecarboxylic acid, characterized in that asymmetric diethylethylenediamine is allowed to act on acid halides of 2-halo-4-quinolinecarboxylic acid and the 2-halo-4-chir #olinecarboxylic acid obtained is Diethylethylene diamide with alkaline agents that are used to introduce the hexyloxy group is implemented. Das 2-n-Hexyloxy-4-chinolinearbonsäure- diäthyläthylendiamid bildet farblose Kristalle vom Schmelzpunkt 73 . Die Base ist in kal tem Petroläther schwer löslich; in warmem Petroläther, wie in den übrigen organischen Lösungsmitteln ist sie leicht löslich. Mit Säu ren gibt sie neutrale, in Wasser leicht lösliche Salze. Die neue Verbindung soll zu therapeuti schen Zwecken Verwendung finden. The 2-n-hexyloxy-4-quinolinearboxylic acid diethylethylenediamide forms colorless crystals with a melting point of 73. The base is sparingly soluble in cold petroleum ether; It is easily soluble in warm petroleum ether, as in the other organic solvents. With acids it gives neutral salts that are easily soluble in water. The new connection is intended to be used for therapeutic purposes.
CH157848D 1931-12-21 1931-12-21 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH157848A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH157848T 1931-12-21
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH157848A true CH157848A (en) 1932-10-15

Family

ID=25712964

Family Applications (1)

Application Number Title Priority Date Filing Date
CH157848D CH157848A (en) 1931-12-21 1931-12-21 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid.

Country Status (1)

Country Link
CH (1) CH157848A (en)

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