CH139441A - 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
CH139441A
CH139441A CH139441DA CH139441A CH 139441 A CH139441 A CH 139441A CH 139441D A CH139441D A CH 139441DA CH 139441 A CH139441 A CH 139441A
Authority
CH
Switzerland
Prior art keywords
preparation
carboxylic acid
basic derivative
quinolinecarboxylic acid
quinoline carboxylic
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 CH139441A publication Critical patent/CH139441A/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          Chinolincarbonsäure.       Es wurde     gefunden,        dass\        man.    zu einem  basischen Derivat einer     substituierten        Chi-          nolincarbons,äure    gelangt,     wenn,

      man auf       Säurehalogenide    der     2-galogen-4-chinolin-          carbonsäure        asymmetrisches        Dimethyläthy-          lendiamin    einwirken lässt und das     erhaltene          2-Halogen    - 4 =     ehinolincar1)onsäure-dimethyl-          äthylendiamid    mit alkalischen     Äthogylie-          rungsmitteln    umsetzt.  



       Dae        2-Äthoxy-4-chinolincarbons5,ure-di-          methyläthylendiamid    bildet farblose Kri  stalle vom Schmelzpunkt<B>127'.</B> Die Base  lässt sich aus     Benzol        umkristallisieren.        Alit     Säuren gibt sie     neutrale,    in Wasser leicht  lösliche Salze.  



  Die neue Verbindung soll zu therapeu  tischen Zwecken Verwendung finden.  <I>Beispiel:</I>  Zu einer Lösung von 0,9 Teilen asym  metrischem     Dimethyläthylendiamin    in 45  Teilen     1-0%iger    Natronlauge gibt man unter    Kühlung und ständigem     Umrühren    allmäh  lich eine     benzolische    Lösung von 2,2 Teilen  2 - Chlor - 4     -!chinolincarimnsäurechlorid        zii.     Nach beendigter     Reaktion    wird die     benzo-          lisehe    Lösung abgetrennt, die gebildete Base  mit Salzsäure ausgezogen und mit Soda wie  der ausgefällt.

   Man nimmt die Base in Ben  zol auf, vertreibt das Lösungsmittel und kri  stallisiert sie aus     Ligroin    um. Das     2-Chlor-          4-chinolincarbonsäure-dimethyläthylendiamid     bildet farblose,     blättrige        Kristalle    vom  Schmelzpunkt 109  . In den     meisten    orga  nischen     Lösungsmitteln    ist die Base leicht  löslich; mit Säuren bildet sie     neutrale,    wasser  lösliche     Salze.     



  17 Teile     2-Chlor-4-chinolinearbonsäure-          dimethyläthylendia-mid    werden mit einer  Lösung von 1,5 Teilen Natrium in     Äthyl-          alkohol    gekocht. Hierauf wird der     Äthyl-          alkohol        abdestilliert,    der Rückstand in Ben  zol aufgenommen und mit     Wasser    ge  waschen. Nach     Entfernung    des Lösungs-      mittels verbleibt das     2-Äthoxy-4-chinolin-          carbonsäure-dimethy#1äthylendiamid    in farb  losen Kristallen.

   Die Base     lässt    sieh aus     Ben-          zol        umkristallisieren.     



  Zur     Einführung    der     Äthoxygruppe    kön  nen auch - andere     Metalläthylate    in orga  nischen Lösungsmitteln oder zum Beispiel  auch     Alkalien    in Gegenwart von     Äthylalko-          hol        Verwendung    finden.



  Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. It was found that \ man. a basic derivative of a substituted quinoline carboxylic acid is obtained if

      asymmetric dimethylethylenediamine is allowed to act on acid halides of 2-galogen-4-quinolinecarboxylic acid and the 2-halo-4 = ehinolinecar1) acid dimethylethylenediamide obtained is reacted with alkaline ethogyling agents.



       The 2-ethoxy-4-quinoline-carbons5, ure-dimethylethylenediamide forms colorless crystals with a melting point of <B> 127 '. </B> The base can be recrystallized from benzene. Alit acids give them neutral salts that are easily soluble in water.



  The new connection is intended to be used for therapeutic purposes. <I> Example: </I> To a solution of 0.9 parts of asymmetrical dimethylethylenediamine in 45 parts of 1-0% sodium hydroxide solution, a benzene solution of 2.2 parts of 2 - chlorine - is gradually added with cooling and constant stirring 4 -! Quinoline carimic acid chloride zii. After the reaction has ended, the benzolisehe solution is separated off, the base formed is extracted with hydrochloric acid and precipitated again with soda.

   The base is taken up in benzene, the solvent is driven off and it is crystallized from ligroin. The 2-chloro-4-quinolinecarboxylic acid dimethylethylenediamide forms colorless, leafy crystals with a melting point of 109. The base is easily soluble in most organic solvents; with acids it forms neutral, water-soluble salts.



  17 parts of 2-chloro-4-quinolinearboxylic acid dimethylethylenediamide are boiled with a solution of 1.5 parts of sodium in ethyl alcohol. The ethyl alcohol is then distilled off, the residue is taken up in benzene and washed with water. After removing the solvent, the 2-ethoxy-4-quinoline-carboxylic acid-dimethyl-ethylenediamide remains in colorless crystals.

   The base can be recrystallized from benzene.



  Other metal ethylates in organic solvents or, for example, alkalis in the presence of ethyl alcohol can also be used to introduce the ethoxy group.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolincar- bonsäure, dadurch gekennzeichnet, da.ss man auf .Säureh-alogeriide der 2-HaJogen-4-c'hino- lincarbonsäure asymmetrisches Dim,ethyl- äthy'len.diamineinwirken läss,t und .das erhal tene 2-Halogen-4-chinolincarbonsäure-, PATENT CLAIM: A process for the preparation of a basic derivative of a substituted quinolinecarboxylic acid, characterized in that asymmetric dim, ethyl-ethyl-ethy-len.diamine is allowed to act on. t and .the obtained 2-halo-4-quinolinecarboxylic acid, dime- thylä.thylendiamid mit alkalischen Äthoxy- lierungsmitteln umsetzt. Das 2-Äthoxy-4-chinolincarbons;äure-di- methyläthylendia,mid bildet farblose Kri stalle vom Schmelzpunkt<B>127'.</B> Die Base lässt sich aus Benzol umkristallisieren. Mit .Säuren gibt sie neutrale, in Wasser leicht lös liche Salze. Die neue Verbindung soll zu therapeu tischen Zwecken Verwendung finden. Dimethylä.thylenediamid with alkaline ethoxylating agents. The 2-ethoxy-4-quinolinecarboxylic acid-dimethylethylenediamide forms colorless crystals with a melting point of <B> 127 '. </B> The base can be recrystallized from benzene. With acids it gives neutral salts that are easily soluble in water. The new connection is intended to be used for therapeutic purposes.
CH139441D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139441A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139441T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139441A true CH139441A (en) 1930-04-15

Family

ID=25712951

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139441D CH139441A (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) CH139441A (en)

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