CH139424A - 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
CH139424A
CH139424A CH139424DA CH139424A CH 139424 A CH139424 A CH 139424A CH 139424D A CH139424D A CH 139424DA CH 139424 A CH139424 A CH 139424A
Authority
CH
Switzerland
Prior art keywords
acid
preparation
petroleum ether
carboxylic acid
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 CH139424A publication Critical patent/CH139424A/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)
  • Quinoline Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines basischen Derivates einer substituierten       Chinolinear    Bonsäure.    Es wurde gefunden,     .dass    man zu einem  basischen Derivat einer     substituierten        Chino-          linca.rbonsäure        gelangt,    wenn man auf       Säureha.logenide    der     2-Halogen-4-chinolin-          carbonsäure    asymmetrisches     Diäthyläthylen-          dia.min    einwirken lässt und das erhaltene       2-Hal        ogen-4-chinolinearbonsäure-diä,thyl,

  äthy-          lendiamid    mit alkalischen     Mitteln,    die zur  Einführung der     n-Butyloxygruppe    dienen,  umsetzt.  



  Das     2-n-Butyloxy-4-chinolinearbonsäure-          diäthyläthylendiamid    bildet farblose Kri  stalle vom Schmelzpunkt 64'. Die Base ist.  in kaltem     Petroläther    schwer löslich;     in    war  mem     Petroläther,    wie in den     übrigen    orga  nischen     Lösungsmitteln    ist sie leicht löslich.  Mit Säuren gibt ,sie neutrale, in Wasser  leicht lösliche     Salze.     



  Die neue Verbindung soll zu therapeu  tischen Zwecken     Verwendung    finden.       Beispiel:     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-chinolinearbonsäurechlorid    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 kri  stallisiert sie aus     Petroläther    um. Das       2-Chlor-4-chinolincarbonsäurediäthyläthylen-          diamid        bildet    farblose, blättrige Kristalle  vom     Schmelzpunkt    74'. In den meisten or  ganischen Lösungsmitteln ist die Base leicht  löslich; mit     Säuren.    bildet sie neutrale, was  serlösliche Salze.  



  12 Teile     2-Chlor-4-ehinolinc.arbonsäure-          diäthyläthylendiamid    werden mit einer Lö  sung von 1 Teil     Natrium    in     n-Butylalkoh.ol     gekocht. Hierauf     -wird    der     n-Butyialkohol          abdestilliert,    der Rückstand in Äther auf  genommen und mit Wasser gewaschen. Nach  Entfernung des     Lösungsmittels    verbleibt das           2-n-Butyloxy-4-chinolincarbons,äure-diäthyl-          äthylendiamid    als Öl, das alsbald zu farb  losen     Kristallen    erstarrt.

   Die Base lässt sich  aus     Petrol_äther        umkristal:lisieren.     



  Zur     Einführung    der     n-Butyloxygruppe     können auch andere     Metall-n-butylate    in or  ganischen Lösungsmitteln oder zum Beispiel  auch Alkalien in Gegenwart von     n-Butyl-          alkohol    Verwendung finden.



  Process for the preparation of a basic derivative of a substituted quinolinear bonic acid. It has been found that .that one arrives at a basic derivative of a substituted quinolinecarboxylic acid if asymmetric diethylethylene dia.min is allowed to act on Säureha.logenide of 2-halo-4-quinolinecarboxylic acid and the resulting 2-Hal ogen-4-quinolinearboxylic acid-diä, thyl,

  Ethylenediamide with alkaline agents, which serve to introduce the n-butyloxy group, reacts.



  The 2-n-butyloxy-4-quinolinearboxylic acid diethylethylenediamide forms colorless crystals with a melting point of 64 '. The base is. Hardly soluble in cold petroleum ether; In war mem petroleum ether, as in the other organic solvents, it is easily soluble. With acids there are neutral salts that are easily soluble in water.



  The new connection is intended to be used for therapeutic purposes. Example: 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-quinolinearboxyl chloride is gradually added 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-quinolincarboxylic acid diethylethylene diamide 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.



  12 parts of 2-chloro-4-ehinolinc.arbonsäure- diethyläthylendiamid are boiled with a solution of 1 part of sodium in n-Butylalkoh.ol. The n-butyl alcohol is then distilled off, the residue is taken up in ether and washed with water. After the solvent has been removed, the 2-n-butyloxy-4-quinoline-carboxylic acid, diethyl-ethylenediamide remains as an oil, which soon solidifies to form colorless crystals.

   The base can be recrystallized from petroleum ether.



  Other metal n-butylates in organic solvents or, for example, alkalis in the presence of n-butyl alcohol can also be used to introduce the n-butyloxy group.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolincar- bonsäure, dadurch gekennzeichnet dass man auf Säurehalogenide der 2-Halogen-4-chino- lincarbonsäure asymmetrisches Diäthyläthy- lendiamin einwirken lä,sst und das erhaltene 2-I3alogen-4-chinolinearbonsäure-diäthyläthy- lendiamid mit alkalischen Mitteln, die zur Einführung der n-Butyloxyo-ruppe 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 2-13alogen-4-quinolinearboxylic acid diethylethyl obtained is allowed to act - Lendiamid with alkaline agents that are used to introduce the n-butyloxyo group, converts. Das 2-n-Butyloxy-4-chinolinea.rbonsä.ure- diäthyläthylendiamid bildet farblose Kristalle vom Sehmelzpunkt 64'. 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 therapeu tischen Zwecken Verwendung finden. The 2-n-butyloxy-4-quinolinea.rbonsä.ure- diethylethylenediamide forms colorless crystals with a melting point of 64 '. The base is sparingly soluble in cold petroleum ether; in warm petroleum ether, as in other organic solvents, it is easily soluble. With acids it gives neutral, easily soluble salts in water. The new connection is intended to be used for therapeutic purposes.
CH139424D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139424A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139424T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139424A true CH139424A (en) 1930-04-15

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ID=25712934

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139424D CH139424A (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) CH139424A (en)

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