CH191459A - Process for the preparation of a carboxamide containing a pyridine nucleus. - Google Patents

Process for the preparation of a carboxamide containing a pyridine nucleus.

Info

Publication number
CH191459A
CH191459A CH191459DA CH191459A CH 191459 A CH191459 A CH 191459A CH 191459D A CH191459D A CH 191459DA CH 191459 A CH191459 A CH 191459A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
preparation
pyridine nucleus
acid dimethylamide
catalysts
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 CH191459A publication Critical patent/CH191459A/en

Links

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

  

      Verfahren    zur Darstellung eines den     Pyridinkern    enthaltenden     Carbonsänreamides.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Darstellung     eines    den       Pyridinkern    enthaltenden     Carbonsäureami-          des,        welches-    dadurch gekennzeichnet ist, dass  man auf ein     2-Halogen-chinolin-4-carbon-          säuredimethylamid        katalytisch    angeregten  Wasserstoff einwirken lässt.  



  Das so erhaltene     Chinolin-4-carbonsäure-          dimethylamid    bildet ein dickes, farbloses 01  vom     Kpo"g1@50    bis:     152     . Die neue Verbin  dung soll therapeutische     Verwendung    finden.

         Beispiel:     Eine Lösung von 47 Teilen     2-Chlorchino-          lin-4-earbonsäuredimethylamid    in 400 Teilen       Dioaan    und 50 Teilen 20%iger Natronlauge  wird in     Gegenwart    von aktivem Nickel bei  40' mit Wasserstoff     reduziert.    Nach be  endigter Wasserstoffaufnahme wird das,     Lö-          sungsmittel    im Vakuum     abdestilliert,    der  Rückstand mit Äther ausgezogen, die Äther  lösung mit wenig Wasser gewaschen,

   ge  trocknet und     eingedampft.    Man     erhä.l.t        Glas            Chinolin    - 4 -     carbonsäure        -.dimethylamid    als  dickes, farbloses     Q01    vom     gpo.o3150    bis 152  .  



  An Stelle des     Diogans    können auch     ali-          phatische    Alkohole und statt Natronlauge       aliphatische    Amine und     Pyridin    als säure  bindende     Mittel    verwendet werden.  



  Statt mit     2-Chlorchinolin-4-carbonsäure-          dimethylamid    kann man die     Reaktion    auch  mit einem     andern        2-Halogen-chinolin-4-car-          bonsäuredimethylamid        ausführen.     



  Als Katalysatoren können ausser Nickel  z.     B.    auch Kobalt, Gemische von Nickel und  Kobalt, sowie Platin, Palladium und     dergl.     angewandt werden.



      Process for the preparation of a carbonic acid amide containing the pyridine nucleus. The present patent relates to a process for the preparation of a carboxamide containing the pyridine nucleus, which is characterized in that catalytically excited hydrogen is allowed to act on a 2-haloquinoline-4-carboxylic acid dimethylamide.



  The quinoline-4-carboxylic acid dimethylamide obtained in this way forms a thick, colorless oil from Kpo "g1 @ 50 to: 152. The new compound is intended to find therapeutic use.

         Example: A solution of 47 parts of 2-chloroquinoline-4-carboxylic acid dimethylamide in 400 parts of dioan and 50 parts of 20% strength sodium hydroxide solution is reduced with hydrogen at 40 'in the presence of active nickel. After the hydrogen uptake is complete, the solvent is distilled off in vacuo, the residue is extracted with ether, the ether solution is washed with a little water,

   ge dried and evaporated. A glass of quinoline-4-carboxylic acid dimethylamide is obtained as a thick, colorless Q01 from gpo.o3150 to 152.



  Aliphatic alcohols and instead of sodium hydroxide solution aliphatic amines and pyridine can also be used as acid-binding agents in place of the diogan.



  Instead of using 2-chloroquinoline-4-carboxylic acid dimethylamide, the reaction can also be carried out with another 2-haloquinoline-4-carboxylic acid dimethylamide.



  As catalysts, in addition to nickel, for. B. cobalt, mixtures of nickel and cobalt, as well as platinum, palladium and the like. Can be used.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines. den Py- ridinkern enthaltenden Carbonsäureamides, dadurch gekennzeichnet, dass man auf ein 2 Halogen-chinolin-4-carbonsäuredimethylamid katalytisch angeregten Wasserstoff einwir ken lässt, Das so erhaltene Chinolin-4-carbonsäure- dimethylamid bildet ein dickes, farbloses 01 vom Kpa,os150 bis 152 . Die neue Verbin dung soll therapeutische Verwendung finden. PATENT CLAIM: Method for representing a. the carboxamides containing the pyridine nucleus, characterized in that catalytically excited hydrogen is allowed to act on a 2 haloquinoline-4-carboxylic acid dimethylamide. The quinoline-4-carboxylic acid dimethylamide thus obtained forms a thick, colorless oil from Kpa, os150 to 152. The new connec tion should find therapeutic use. UNTERANSPRüCHE: 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Katalysa toren Metalle der Platingruppe verwendet. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, .dass, man als Katalysa- toren unedle Metalle verwendet. Verfahren nach Patentanspruch, dadurch gekennzeichnet,' dass man als Katalysator Nickel verwendet. 4. SUBClaims: 1. Method according to claim, characterized in that platinum group metals are used as catalysts. 2. The method according to claim, characterized in .dass, base metals are used as catalysts. Process according to claim, characterized in that the catalyst used is nickel. 4th Verfahren nach Patentauspruch, dadurch gekennzeichnet, ,dass man in Gegenwart säurebindender Mittel arbeitet. Process according to patent claim, characterized in that one works in the presence of acid-binding agents.
CH191459D 1934-11-24 1934-11-24 Process for the preparation of a carboxamide containing a pyridine nucleus. CH191459A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH186664T 1934-11-24
CH191459T 1934-11-24

Publications (1)

Publication Number Publication Date
CH191459A true CH191459A (en) 1937-06-15

Family

ID=25721399

Family Applications (1)

Application Number Title Priority Date Filing Date
CH191459D CH191459A (en) 1934-11-24 1934-11-24 Process for the preparation of a carboxamide containing a pyridine nucleus.

Country Status (1)

Country Link
CH (1) CH191459A (en)

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