CH139427A - 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
CH139427A
CH139427A CH139427DA CH139427A CH 139427 A CH139427 A CH 139427A CH 139427D A CH139427D A CH 139427DA CH 139427 A CH139427 A CH 139427A
Authority
CH
Switzerland
Prior art keywords
acid
preparation
carboxylic acid
quinolinecarboxylic acid
petroleum ether
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 CH139427A publication Critical patent/CH139427A/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)
  • Plural Heterocyclic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines basiseben Derivates einer substituierten       Cbinoiinearbonsäur    e.    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    -     chinolinearbonsäure    -     diäthyläthylendiamid          finit    alkalischen Mitteln,

   die zur Einführung  der     Isoamyloxygruppe    dienen, umsetzt.  



  Das 2 -     Isoamyloxy-4-chinolincarbonsäure-          diäthyläthylendiamid    bildet farblose Kristalle  vom     Smp.    35 0. Die Base ist in kaltem     Petrol-          äther    schwer löslich; in warmem     Petroläther,     wie in den übrigen organischen Lösungs  mitteln ist sie leicht löslich. Mit Säuren gibt  sie neutrale, in Wasser leicht lösliche Salze.  



  Die neue Verbindung soll zu therapeuti  schen Zwecken Verwendung finden.       Beispiel:     Zu einer Lösung von 1,2 Teilen asym  metrischem     Diäthyläthylendiamin    in 45 Tei-         len        10        %iger        Natronlauge        gibt        man        unter     Kühlung und ständigem Umrühren allmählich  eine     benzolische    Lösung von 2,2 Teilen     2-          Chlor-4-chinolincarbonsäurechlorid    zu.

   Nach  beendigter 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 kristal  lisiert sie aus     Petroläther    um. Das     2-Chlor-          4    -     chinolincarbonsäure    -     diätbyläthylendiamid     bildet farblose, blätterige Kristalle vom     Smp.     740. In den meisten organischen Lösungsmit  teln ist die Base leicht löslich; mit Säuren  bildet sie neutrale,     wasserlöliche    Salze.  



  12 Teile 2 - Chlor - 4 -     chinolincarbonsäure-          diäthyläthylendiamid    werden mit einer Lösung  von 1 Teil Natrium in     Isoamylalkohol    gekocht.  Hierauf wird der     Isoamylalkohol    im Vakuum       abdestilliert,    der Rückstand in Äther aufge  nommen und mit Wasser gewaschen. Nach  Entfernung des Lösungsmittels verbleibt das      2 -     Isoamyloxy    - 4 -     chinolincarbon        säure-diäthyl-          äthylendiamid    als Öl, das alsbald zu farb  losen Kristallen erstarrt.

   Die Base lässt sich  aus     Petrol.äther        umkristallisieren.     



  Zur Einführung der     Isoamyloxygruppe     können auch andere     Metall-iso-amylate    in  organischen Lösungsmitteln oder zum Beispiel  auch Alkalien in Gegenwart von     Isoamyl-          alkohol    Verwendung finden.



  Process for the preparation of a basic derivative of a substituted Cbinoiinearbonsäur e. It has been found that a basic derivative of a substituted quinolinecarboxylic acid is obtained if asymmetric diethylethylenediamine is allowed to act on acid halides of 2-halo-4-quinolinecarboxylic acid and the 2-halo-4-quinolinearboxylic acid obtained is finitely alkaline with diethylethylenediamide Means,

   which serve to introduce the isoamyloxy group, converts.



  The 2-isoamyloxy-4-quinolinecarboxylic acid diethylethylenediamide forms colorless crystals with a melting point of 35 0. The base is sparingly soluble in cold petroleum ether; it is easily soluble in warm petroleum ether, as in other organic solvents. With acids it gives neutral, easily soluble salts in water.



  The new connection is intended to be used for therapeutic purposes. Example: A benzene solution of 2.2 parts of 2-chloro-4-quinolinecarboxylic acid chloride is gradually added to a solution of 1.2 parts of asymmetrical diethylethylenediamine in 45 parts of 10% strength sodium hydroxide solution, with cooling and constant stirring.

   After the reaction has ended, 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 crystallized from petroleum ether. The 2-chloro-4 - quinoline carboxylic acid - dietbylethylenediamide forms colorless, leafy crystals with a melting point of 740. The base is easily soluble in most organic solvents; with acids it forms neutral, water-soluble salts.



  12 parts of 2-chloro-4-quinoline-carboxylic acid diethylethylenediamide are boiled with a solution of 1 part of sodium in isoamyl alcohol. The isoamyl alcohol is then distilled off in vacuo, the residue is taken up in ether and washed with water. After removal of the solvent, the 2 - isoamyloxy - 4 - quinolincarboxylic acid diethyl ethylenediamide remains as an oil, which soon solidifies to form colorless crystals.

   The base can be recrystallized from petroleum ether.



  Other metal iso-amylates in organic solvents or, for example, alkalis in the presence of isoamyl alcohol can also be used to introduce the isoamyloxy group.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolincarbon- säure, dadurch gekennzeichnet, dass man auf Säurehalogenide der 2-Halogen-4-chinolinear- bonsäure asymmetrisches Diäthyläthylendi- amin einwirken lässt und das erhaltene 2-Ha- logen -4-chinolincarbonsäure-diäthyläthylendi- amid mit alkalischen Mitteln, die zur Einfüh rung der Isoamyloxygruppe dienen, umsetzt. PATENT CLAIM: A 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-halogen-4-quinolinearboxic acid and the 2-halogen-4-quinolinecarboxylic acid obtained is Diethyläthylendi- amid with alkaline agents that are used to introduce the isoamyloxy group, implements. Das 2-Isoamyloxy-4-chinolincarbonsäure- diäthyläthylendiamid bildet farblose Kristalle vom Smp. 35 . Die Base ist in kaltem Petrol- äther schwer löslich; in warmem Petroläther, wie in den übrigen organischen Lösungs mitteln ist sie leicht löslich. Mit Säuren gibt sie neutrale, in Wasser leicht lösliche Salze. Die neue Verbindung soll zu therapeuti schen Zwecken Verwenndug finden. The 2-isoamyloxy-4-quinolinecarboxylic acid diethylethylenediamide forms colorless crystals with a melting point of 35. The base is sparingly soluble in cold petroleum ether; it is easily soluble in warm petroleum ether, as in other organic solvents. With acids it gives neutral, easily soluble salts in water. The new compound is intended to be used for therapeutic purposes.
CH139427D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139427A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139427T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139427A true CH139427A (en) 1930-04-15

Family

ID=25712937

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139427D CH139427A (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) CH139427A (en)

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