CH139439A - 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
CH139439A
CH139439A CH139439DA CH139439A CH 139439 A CH139439 A CH 139439A CH 139439D A CH139439D A CH 139439DA CH 139439 A CH139439 A CH 139439A
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 CH139439A publication Critical patent/CH139439A/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       Chinolincarbonsäure.       Es wurde gefunden,     d.ass    man zu einem  .basischen Derivat einer     substituierten        Chino-          linca.rbonsäure    gelangt, wenn man auf Säure  halogenide der     '2-Halogen,.4-chinolincaVbon-          säure        Triäthyläthylendiamin    einwirken lässt  und das erhaltene     2-I-aI.ogen-4-chinolincar-          bonsäure-triäthylä.thy        lendiamid    mit Mitteln,

    die zur Einführung der     Benzyloxygruppe     dienen, umsetzt.  



  Das     2-Benzyloxy-4-chinolinearbonsäure-          triäthyläthylendiamid    bildet ein hellgelbes  01 vom     Siedepunkt    19,2   bei 0,01 ,mm Druck.  Die Base ist in organischen Lösungsmitteln  leicht     löslich.    Mit     iSäuren    gibt sie neutrale,  in Wasser leicht lösliche     .Salze.     



  Die neue Verbindung soll zu therapeu  tischen Zwecken Verwendung     finden.          Beispiel:     Zu einer Lösung von 1,5 Teilen     Triärthyl-          äthylendiamin    (farblose Base vom     Siedepunkt     160-165  , dargestellt durch     Reduktion    des    Kondensationsproduktes aus     as.        Diä@thyläthy-          lendiamin    und     Acetaldehyd    vom Siedepunkt  40   bei 7 mm Druck) in 4 Teilen 10     %iger          Natronlauge    lässt man unter Rühren und  Kühlen eine     benzolische    Lösung von 2,

  2 Tei  len     2-Chlor-4-chinolincarbonsä.urechlorid    all  mählich zufliessen. Nach beendeter Reaktion  wird mit Wasser     gewaschen        und,das    Lösungs  mittel     abdestilliert.    Das     2-Chlor-4-chinolin-          carbonsäure-triäthyläthylendiami-d    bildet ein  gelbliches Öl vom Siedepunkt 16,5   bei etwa  0,015 mm Druck. In organischen Lösungs  mitteln ist es leicht löslich. Mit Säuren gibt  die Base neutrale, wasserlösliche Salze.  



  2,5 Teile Natrium werden mit 1.3 Teilen       Benzylalkohol    durch Erwärmen in     Toluol-          lösun,g    umgesetzt. Hierauf gibt man 30 Teile  2 -     Chlor-        4-chinalincarbonsäure-        triäthyläthy-          lendiamid    hinzu und     erwärmt    im Ölbad bis  zur Beendigung der Reaktion. Man wäscht  mit Wasser aus und     destilliert    das Lösungs  mittel im Vakuum ab. Man erhält -das           2-Benzy        loxy-4-chinolincarbonsäure-triäthyl-          äthylendiamid    als hellgelbes 01.

   Die Base  lässt sich im Vakuum destillieren.  



  Zur Einführung der     Benzyloxygruppe     können auch andere     Metallbenzylate    in or  ganischen     Lösungsmitteln    oder zum Beispiel  Alkalien in Gegenwart von     Benzylalkohol     Verwendung finden.



  Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. It has been found that a .basic derivative of a substituted quinolinecarboxylic acid is obtained if triethylethylenediamine is allowed to act on acid halides of the '2-halogen, .4-quinolinecarboxylic acid and the 2-I-aI obtained .ogen-4-quinolinecarbonsäure-triäthylä.thy lendiamid with agents,

    which serve to introduce the benzyloxy group, converts.



  The 2-benzyloxy-4-quinolinearboxylic acid triethylethylenediamide forms a light yellow oil with a boiling point of 19.2 at a pressure of 0.01 mm. The base is easily soluble in organic solvents. With i-acids it gives neutral, easily soluble salts in water.



  The new connection is intended to be used for therapeutic purposes. Example: To a solution of 1.5 parts of triethylethylenediamine (colorless base with a boiling point of 160-165, produced by reducing the condensation product of as. Diethylethylenediamine and acetaldehyde with a boiling point of 40 at 7 mm pressure) in 4 parts of 10% iger sodium hydroxide solution is left with stirring and cooling a benzene solution of 2,

  Gradually add 2 parts of 2-chloro-4-quinolincarboxylic acid chloride. After the reaction has ended, it is washed with water and the solvent is distilled off. The 2-chloro-4-quinoline-carboxylic acid-triäthyläthylendiami-d forms a yellowish oil with a boiling point of 16.5 at about 0.015 mm pressure. It is easily soluble in organic solvents. With acids, the base gives neutral, water-soluble salts.



  2.5 parts of sodium are reacted with 1.3 parts of benzyl alcohol by heating in toluene solution. 30 parts of 2-chloro-4-quinaline-carboxylic acid triethylethylenediamide are then added and the mixture is heated in an oil bath until the reaction has ended. It is washed with water and the solvent is distilled off in vacuo. The 2-Benzy loxy-4-quinolinecarboxylic acid triethyl ethylenediamide is obtained as a light yellow 01.

   The base can be distilled in vacuo.



  Other metal benzylates in organic solvents or, for example, alkalis in the presence of benzyl alcohol can also be used to introduce the benzyloxy group.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolincar- bonsäure, dadurch gekennzeichnet, da.ss man auf Säurehalogenide der 2-Halogen-4-chino- lincarbonsäure Triäthyläthylendiamin ein- wirken lässt und das erhaltene 92-Halogen- 4 -chinolincarbonsäure-.triäthyläthylen.diamid mit Mitteln, idie zur Einführung der Benzyl- oxygruppe dienen, umsetzt. PATENT CLAIM: Process for the preparation of a basic derivative of a substituted quinolinecarboxylic acid, characterized in that the acid halides of 2-halo-4-quinolinecarboxylic acid triethylethylenediamine are allowed to act and the 92-halo-4-quinolinecarboxylic acid obtained. triäthyläthylen.diamid with agents which serve to introduce the benzyl oxy group. Das 2-Benzyloxy-4-chinolinearbonsä,ure- triäthyläthylen.diamid bildet ein hellgelbes 01 vom 'Siedepunkt 19',2" bei 0,01 'mm Druek. Die Base ist in organischen Lösungsmitteln leicht löslich. Mit iSäuren gibt sie neutrale, in Wasser leicht lösliche Salze. Die neue Verbindung soll zu therapeu tischen Zwecken Verwendung finden. The 2-benzyloxy-4-quinolinearbonsä, ure- triäthyläthylen.diamid forms a light yellow 01 with a 'boiling point 19', 2 "at 0.01 'mm pressure. The base is easily soluble in organic solvents. With iAids it gives neutral, in Easily soluble salts in water.The new compound is said to be used for therapeutic purposes.
CH139439D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139439A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139439T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139439A true CH139439A (en) 1930-04-15

Family

ID=25712949

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139439D CH139439A (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) CH139439A (en)

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