CH156355A - Process for the preparation of a basic substituted carboxamide. - Google Patents

Process for the preparation of a basic substituted carboxamide.

Info

Publication number
CH156355A
CH156355A CH156355DA CH156355A CH 156355 A CH156355 A CH 156355A CH 156355D A CH156355D A CH 156355DA CH 156355 A CH156355 A CH 156355A
Authority
CH
Switzerland
Prior art keywords
preparation
dimethyl
substituted carboxamide
basic substituted
butyloxy
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 CH156355A publication Critical patent/CH156355A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

      Verfahren    zur     Herstellung    eines basisch substituierten     Carbonsäureamids.       Es wurde gefunden, dass man zu einem  basisch substituierten     Carbonsäureamid    ge  langen kann, wenn man einen reaktionsfähi  gen Ester des     2-Dimethyl-3-diäthylaminopro-          panols    auf ein Metallderivat des     2-n-Butyl-          oxy-4-ohinolincarbonsäureamids    einwirken  lässt.  



  Das so erhaltene     2-n-Butyloxy-4-chinolin-          carbonsäure    - 2 -     dimethyl        -1,3-diäthylpropylen-          diamid    ist ein gelbes Öl, das in organischen  Lösungsmitteln leicht löslich ist.  



  Die neue Verbindung soll entweder als  solche oder in Form ihrer Salze zu techni  schen und therapeutischen Zwecken Verwen  dung finden.    <I>Beispiel:</I>  4,9 Teile     2-n-Butyloxychinolincarbonsäure-          amid    (farblose Kristalle vom     Smp.        160-1610,     dargestellt aus     2-Chlor-4-chinolincarbonsäur-e-          amid    und einer Lösung von Natrium in     Bu-          tylalkohol)    werden in 100 Teilen     Toluol    mit    0,8 Teilen     Natriumamid    bis zur Beendigung  der     Ammoniakentwicklung    erwärmt.

   Nun  fügt man 3,6 Teile     2-Dimethyl-3-chlor-diäthyl-          propylamin    (ölige Base vom     Sdp.ii    69-70 ;  dessen Chlorhydrat vom     Smp.    109   erhält  man aus     2-Dimethyl-3-diäthylaminopropanol     mit     Thionylchlorid)    zu und erwärmt weiter.  Nach erfolgter Umsetzung wird die Base mit  verdünnter Säure ausgezogen, aus der wäs  serigen Lösung mit Soda gefällt und     ausge-          äthert;    durch Vertreiben des Lösungsmittels  erhält man die Base als gelbes Öl.  



  An Stelle von     2-Dimethyl-3-chlordiäthyl-          propylamin    können auch andere reaktions  fähige Ester des     2-Dimethyl-3-diäthylamino-          propanols,    zum Beispiel der Bromwasserstoff-,  der     Jodwasserstoff    oder der     Toluolsulfosäure-          ester    Verwendung finden.

   Zur Herstellung  der Metallverbindung des     Carbonsäureamids     kann man auch andere     Metallamide,    wie zum  Beispiel Kalium- oder     Calciumamid,    Metall  alkoholate, wie zum Beispiel     Natrium-          oder        Kaliumalkoholat    oder reaktionsfähige      Metalle wie zum Beispiel Natrium, Kalium  usw. gebrauchen.



      Process for the preparation of a basic substituted carboxamide. It has been found that a base-substituted carboxamide can be obtained if a reactive ester of 2-dimethyl-3-diethylaminopropanol is allowed to act on a metal derivative of 2-n-butyloxy-4-ohinolinecarboxamide.



  The 2-n-butyloxy-4-quinoline-carboxylic acid 2-dimethyl -1,3-diethylpropylene diamide obtained in this way is a yellow oil which is easily soluble in organic solvents.



  The new compound is said to be used either as such or in the form of its salts for technical and therapeutic purposes. <I> Example: </I> 4.9 parts of 2-n-butyloxyquinolinecarboxylic acid amide (colorless crystals with a melting point of 160-1610, made from 2-chloro-4-quinolinecarboxylic acid amide and a solution of sodium in Bu - tyl alcohol) are heated in 100 parts of toluene with 0.8 parts of sodium amide until the evolution of ammonia has ended.

   Now 3.6 parts of 2-dimethyl-3-chloro-diethylpropylamine (oily base of bp 69-70; its hydrochloride of mp 109 are obtained from 2-dimethyl-3-diethylaminopropanol with thionyl chloride) are added and continues to heat. After the reaction has taken place, the base is extracted with dilute acid, precipitated from the aqueous solution with soda and extracted with ether; by driving off the solvent, the base is obtained as a yellow oil.



  Instead of 2-dimethyl-3-chlorodiethylpropylamine, other reactive esters of 2-dimethyl-3-diethylaminopropanol, for example hydrogen bromide, hydrogen iodide or toluenesulfonic acid esters, can also be used.

   Other metal amides such as potassium or calcium amide, metal alcoholates such as sodium or potassium alcoholate or reactive metals such as sodium, potassium, etc. can also be used to produce the metal compound of the carboxamide.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines basisch substituierten Carbonsäureamids, dadurch ge kennzeichnet, dass man einen reaktionsfähigen Ester des 2-Dimethyl-3-diäthylaminopropanols auf ein Metallderivat des 2-n-Butyloxy-4- chinoliiicarbonsäureamids einwirken lässt. Das so erhaltene 2-n-Butyloxy-9-chinolin- oarbonsäure- 2 -dimethyl-1,3 -diäthylpropylen- diamid ist ein gelbes Öl, das in organischen Lösungsmitteln leicht löslich ist. Claim: A process for the preparation of a basic substituted carboxamide, characterized in that a reactive ester of 2-dimethyl-3-diethylaminopropanol is allowed to act on a metal derivative of 2-n-butyloxy-4-quinoliiicarboxamide. The 2-n-butyloxy-9-quinolin-oarboxylic acid-2-dimethyl-1,3-diethylpropylene diamide thus obtained is a yellow oil which is easily soluble in organic solvents. Die neue Verbindung soll entweder als solche oder in Form ihrer ,Salze zu techni schen- und therapeutischen Zwecken Ver wendung finden. The new compound is said to be used either as such or in the form of its salts for technical and therapeutic purposes.
CH156355D 1930-05-09 1930-05-09 Process for the preparation of a basic substituted carboxamide. CH156355A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH156355T 1930-05-09
CH153033T 1930-05-09

Publications (1)

Publication Number Publication Date
CH156355A true CH156355A (en) 1932-07-31

Family

ID=25716113

Family Applications (1)

Application Number Title Priority Date Filing Date
CH156355D CH156355A (en) 1930-05-09 1930-05-09 Process for the preparation of a basic substituted carboxamide.

Country Status (1)

Country Link
CH (1) CH156355A (en)

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