CH156350A - Process for the preparation of a basic substituted carboxamide. - Google Patents

Process for the preparation of a basic substituted carboxamide.

Info

Publication number
CH156350A
CH156350A CH156350DA CH156350A CH 156350 A CH156350 A CH 156350A CH 156350D A CH156350D A CH 156350DA CH 156350 A CH156350 A CH 156350A
Authority
CH
Switzerland
Prior art keywords
ethoxy
preparation
basic substituted
substituted carboxamide
quinolinecarboxylic
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 CH156350A publication Critical patent/CH156350A/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

      Verfahren    zur Herstellung     eines    basisch     substituierten        Carbonsäureauiids.       Es wurde gefunden, dass man zu einem  basisch substituierten     Carbonsäureamid    ge  langen kann, wenn man einen reaktionsfähi  gen Ester des     Diäthylaminoäthanols    auf ein  Metallderivat des     2-Äthoxy-4-chinolincarbon-          säureanilids    einwirken lässt.  



  Das so erhaltene     2-Äthoxy-4-chinolin-          carbonsäure-    N     -phenyl-    N     -diäthylaminoäthyl-          amid    bildet ein gelbliches Öl, vom Kp. o,5       205-210'.    Das in Wasser schwer lösliche       Perchlorat    der Base schmilzt bei     160-r62     .  



  Die neue Verbindung soll zu therapeuti  schen Zwecken Verwendung finden.  



  <I>Beispiel</I>  8,9 Teile     2-Äthoxy-4-chinolincarbonsäure-          anilid    (farblose Kristalle vom     Smp.        180-1810,     dargestellt aus     2-Chlor-4-chinolincarbonsäure-          anilid    und     äthylalkoholisohem    Natrium) wer  den in 100 Teilen     äylol    mit 1,2 Teilen       Natriumamid    bis zur Beendigung der     Ammo-          niakentwicklung    erwärmt. Nun fügt man    4,1 Teile     Chloräthyldiäthylamin    zu und er  -wärmt weiter.

   Nach erfolgter Umsetzung  destilliert man das Lösungsmittel ab     und     nimmt den Rückstand in verdünnter Säure  auf.     Aus    der filtrierten Lösung wird die  Base mit Soda gefällt und in Äther aufge  nommen. Nach Vertreiben des Lösungsmittels       hinterbleibt    das     2-Äthoxy-4-chinolincarbon-          säure-N-phenyl-N-diäthylaminoäthylamid    als  gelbliches 01 vom     Kp.        o,5        205-2100.     



  An Stelle von     Chloräthyldiäthylamin    kön  nen auch andere reaktionsfähige Ester des       Diäthylaminoäthanols,    zum Beispiel der Brom  wasserstoff-, der     Jodwasserstoff-    oder der       Toluolsulfosäureester    Verwendung finden. Zur  Herstellung der Metallverbindung des     Carbon-          säureamids    kann man auch andere Metall  amide, wie zum Beispiel Kalium- oder     Kal-          ziumamid,        Metallalkoholate,    wie zum Beispiel  Natrium- oder     galiumalkoholat    oder reak  tionsfähige Metalle wie zum Beispiel Natrium,  Kalium usw. gebrauchen.



      Process for the preparation of a basic substituted carboxylic acid eiide. It has been found that a basic substituted carboxamide can be obtained if a reactive ester of diethylaminoethanol is allowed to act on a metal derivative of 2-ethoxy-4-quinolinecarboxylic anilide.



  The 2-ethoxy-4-quinoline-carboxylic acid-N-phenyl-N -diethylaminoethyl amide thus obtained forms a yellowish oil, with a boiling point of 0.5205-210 '. The perchlorate of the base, which is sparingly soluble in water, melts at 160-r62.



  The new connection is intended to be used for therapeutic purposes.



  <I> Example </I> 8.9 parts of 2-ethoxy-4-quinoline-carboxylic acid anilide (colorless crystals with a melting point of 180-1810, prepared from 2-chloro-4-quinoline-carboxylic acid anilide and ethyl alcohol isohem sodium) in 100 Parts of ethylene with 1.2 parts of sodium amide were heated until the evolution of ammonia ceased. Now 4.1 parts of chloroethyl diethylamine are added and the heating continues.

   After the reaction has taken place, the solvent is distilled off and the residue is taken up in dilute acid. The base is precipitated from the filtered solution with soda and taken up in ether. After the solvent has been driven off, the 2-ethoxy-4-quinolinecarboxylic acid N-phenyl-N-diethylaminoethylamide remains as a yellowish oil with a boiling point of 0.5205-2100.



  Instead of chloroethyl diethylamine, other reactive esters of diethylaminoethanol, for example hydrogen bromine, hydrogen iodide or toluenesulfonic acid ester, can also be used. Other metal amides, such as potassium or calcium amide, metal alcoholates such as sodium or galium alcoholate or reactive metals such as sodium, potassium, etc., can also be used to produce the metal compound of the carboxylic acid amide.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines basisch substituierten Carbonsäureamids, dadurch ge kennzeichnet, dass man einen reaktionsfähigen Ester des Diäthylaminoäthanols auf ein Me tallderivat des 2-Äthoxy-4-chinolincarbon- säureanilids einwirken lässt. Das so erhaltene 2-Äthogy-4-chinolincar- bonsäure-N-phenyl-N-diäthylaminoäthylamid bildet ein gelbliches Öl vom Kp. o,5 205-210 . Das in Wasser schwer lösliche Perchlorat der Base schmilzt bei 160-162 . Die neue Verbindung soll zu therapeuti schen Zwecken Verwendung finden. Claim: A process for the production of a basic substituted carboxamide, characterized in that a reactive ester of diethylaminoethanol is allowed to act on a metal derivative of 2-ethoxy-4-quinolinecarboxylic anilide. The 2-ethoxy-4-quinolinecarboxylic acid N-phenyl-N-diethylaminoethylamide thus obtained forms a yellowish oil with a boiling point of 0.5205-210. The perchlorate of the base, which is sparingly soluble in water, melts at 160-162. The new connection is intended to be used for therapeutic purposes.
CH156350D 1930-05-09 1930-05-09 Process for the preparation of a basic substituted carboxamide. CH156350A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH156350T 1930-05-09
CH153033T 1930-05-09

Publications (1)

Publication Number Publication Date
CH156350A true CH156350A (en) 1932-07-31

Family

ID=25716108

Family Applications (1)

Application Number Title Priority Date Filing Date
CH156350D CH156350A (en) 1930-05-09 1930-05-09 Process for the preparation of a basic substituted carboxamide.

Country Status (1)

Country Link
CH (1) CH156350A (en)

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