CH139436A - 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
CH139436A
CH139436A CH139436DA CH139436A CH 139436 A CH139436 A CH 139436A CH 139436D A CH139436D A CH 139436DA CH 139436 A CH139436 A CH 139436A
Authority
CH
Switzerland
Prior art keywords
sep
acid
preparation
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 CH139436A publication Critical patent/CH139436A/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          Chinolinearbonsäure.            E:,    wurde gefunden,     .da.ss    man zu einem  basischen Derivat;

   einer .substituierten     Chino-          lincarbonsä        ure    gelangt, wenn man auf Säure  halogenide der     2-FIalogen-4-ehinolincarbon-          säure        Tiriä.thyläthylendiamin    einwirken     lä.sst     und das erhaltene     2-Halogen-4-chinolinoar-          bonsäure-triäthylätliylendiamid    mit Mitteln,  die zur Einführung der     n-Amyloxygruppe     dienen, umsetzt.  



  Das     2-n-Amyloxy-4-chinolincarbonsKure-          triä,thyläthy        len@diamid        bilidet    ein     hellgeltbes     01 vom Siedepunkt<B>175</B>   bei 0,02 mm Druck.  Die Base ist in organischen     Lösungsmitteln     leicht löslich. Mit Säuren gibt sie neutrale,  in Wasser leicht lösliche Salze.  



  Die neue Verbindung soll zu     therapeu-          iischen        .Zwecken    Verwendung finden.  <I>Beispiel.:</I>       Zu    einer Lösung von 1.5 Teilen     Triäthyl-          äthylendia,min    (farblose Base vom Siedepunkt  160-l65 ", dargestellt durch Reduktion des         Kondensationsproduktes    aus     as.        Diäthyläthy-          len:

  dia.min    und     Acetaldehyd    vom Siedepunkt  0 " bei 7 mm Druck) in 4 Teilen 10     %        iger     Natronlauge     lässt    man unter Rühren und  Kühlen eine     benzolische    Lösung von 2,2  Teilen     2-Chlor-4-chinoli,Tncarbonsäuriechlarict     allmählich zufliessen. Nach beendeter Reak  tion wird mit Wasser gewaschen und das Lö  sungsmittel     abdestilliert.    Das     2-Chlor-4-chi-          nolinca.rbonsäure-triäthyläthylendiamid    bil  det ein gelbliches 01 vom Siedepunkt<B>165'</B>  bei etwa 0,015 mm Druck. In organischen       Lösungsmitteln    ist es leicht löslich.

   Mit Säu  ren     gibt        ;die    Base neutrale,     wasserlöisiliche     Salze.  



  33 Teile     2-Chlor-4-chinolincarbonsäure-          triäthyläthylendiamid    werden mit einer Lö  sung von 2,5 Teilen Natrium in     n-Amyl-          alkohol    gekocht. Hierauf wird der     n-Amyl-          alkohol    im Vakuum     abdestilliert,    der Rück  stand in Äther aufgenommen und mit Wasser  gewaschen. Nach Entfernung des Lösungs-    
EMI0002.0001     
  
    mittels <SEP> verbleibt <SEP> das <SEP> 2-n-Ainyloxy-4-cliinolin  earlio.nsäuretriäthyläthylendiamid <SEP> als <SEP> hell  gelbes <SEP> <B>01.</B> <SEP> Die <SEP> Base <SEP> lässt <SEP> sich <SEP> im <SEP> Vakuum
<tb>  destillieren..
<tb>  



  Zur <SEP> Einführung <SEP> der <SEP> n-Amyloxygruppe
<tb>  hünnen <SEP> auch <SEP> andere <SEP> Metall-n-ämylate <SEP> in <SEP> or  ganischen <SEP> Lösungsmitteln <SEP> oder <SEP> zum <SEP> Beispiel
<tb>  Alkalien <SEP> in <SEP> Gegenwart <SEP> .von <SEP> n-rlinyla.ll@oliol
<tb>  Verwendunü; <SEP> finden.



      Process for the preparation of a basic derivative of a substituted quinolinearboxylic acid. E: it was found that a basic derivative is obtained;

   a .substituierten quinolinecarboxylic acid is obtained if halides of the 2-halogeno-4-ehinolinecarboxylic acid Tiriä.thyläthylenediamine are allowed to act and the resulting 2-halo-4-quinolinoarboxylic acid triethylethylenediamide with agents that for Introduction of the n-amyloxy group is used.



  The 2-n-amyloxy-4-quinolincarboxylic acid, thyläthy len @ diamid forms a light yellow oil with a boiling point of 175 at 0.02 mm pressure. The base is easily soluble in organic solvents. With acids it gives neutral, easily soluble salts in water.



  The new connection should be used for therapeutic purposes. <I> Example: </I> To a solution of 1.5 parts of triethylethylenedia, min (colorless base with a boiling point of 160-165 ", produced by reducing the condensation product from as. Diethylethylene:

  dia.min and acetaldehyde of boiling point 0 "at 7 mm pressure) in 4 parts of 10% sodium hydroxide solution, a benzene solution of 2.2 parts of 2-chloro-4-quinoli, carbonic acid odorant, gradually flowing in, while stirring and cooling. After the reaction has ended The solution is washed with water and the solvent is distilled off. The 2-chloro-4-quinoline-a-carboxylic acid triethylethylenediamide forms a yellowish oil with a boiling point of 165 at a pressure of about 0.015 mm. In organic solvents it is easily soluble.

   With acids there are neutral, water-soluble salts with the base.



  33 parts of 2-chloro-4-quinolinecarboxylic acid triethylethylenediamide are boiled with a solution of 2.5 parts of sodium in n-amyl alcohol. The n-amyl alcohol is then distilled off in vacuo, the residue is taken up in ether and washed with water. After removing the solution
EMI0002.0001
  
    with <SEP> <SEP> the <SEP> 2-n-ainyloxy-4-cliinolin earlio.nsäuretriethyläthylendiamid <SEP> remains as <SEP> light yellow <SEP> <B> 01. </B> <SEP> The < SEP> Base <SEP> allows <SEP> to <SEP> in the <SEP> vacuum
<tb> distill ..
<tb>



  For the <SEP> introduction <SEP> of the <SEP> n-amyloxy group
<tb> hünnen <SEP> also <SEP> other <SEP> metal-n-aemylates <SEP> in <SEP> organic <SEP> solvents <SEP> or <SEP> for example <SEP>
<tb> Alkalis <SEP> in <SEP> presence <SEP> .von <SEP> n-rlinyla.ll@oliol
<tb> use; Find <SEP>.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten Cliinolincarbon- säure, dadurch gekennzeichnet, dass man auf Säurehalogenide der 2-Halogeir-4-cliinolinca.r- bonsäure Tiiäthyläthylendiamin einwirken lässt und das erhaltene 2-Halogen-4-chinolin- carbonsäure-triäthyläthylen.diamid mit Mit teln, die zur Einführung der n-Amyloxy- bruppe dienen, umsetzt. PATENT CLAIM: Process for the preparation of a basic derivative of a substituted cliinolinecarboxylic acid, characterized in that acid halides of 2-halo-4-cliinolinecarbohydrate are allowed to act, and the 2-halo-4-quinolinecarboxylic acid-triethylethylene is allowed to act .diamide with means that are used to introduce the n-amyloxy group, implements. Das 2-n-Amyloxy-4-chinolincarbonsäure- tridthylätlryi.endia,mid bildet ein hellgelbes Ü1 vom Siedepunkt 175 bei 0,02 mm Druck. Die Base ist: in organischen Lösungsmitteln 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-amyloxy-4-quinolincarboxylic acid tridthylätlryi.endia, mid forms a light yellow Ü1 with a boiling point of 175 at 0.02 mm pressure. The base is: Easily soluble in organic solvents. With acids it gives neutral, easily soluble salts in water. The new connection is intended to be used for therapeutic purposes.
CH139436D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139436A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139436T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139436A true CH139436A (en) 1930-04-15

Family

ID=25712946

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139436D CH139436A (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) CH139436A (en)

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