CH142344A - Process for the preparation of an amide of a heterocyclic carboxylic acid. - Google Patents

Process for the preparation of an amide of a heterocyclic carboxylic acid.

Info

Publication number
CH142344A
CH142344A CH142344DA CH142344A CH 142344 A CH142344 A CH 142344A CH 142344D A CH142344D A CH 142344DA CH 142344 A CH142344 A CH 142344A
Authority
CH
Switzerland
Prior art keywords
preparation
carboxylic acid
amide
hydrogenation
tetrahydro
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 CH142344A publication Critical patent/CH142344A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

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

Description

       

  Verfahren zur Darstellung eines     Armdes    einer     heteroeyclisehen        Carbonsäure.       Es wurde gefunden, dass man zu einem       Amid    einer     heterocyclischen        Carbonsäure    ge  langen kann, indem man das     Nicotyl-tetra-          hydro-6-aethoxychinolin    hydriert. Als     Hydrie-          rungsmittel    sind zum Beispiel     Wasserstoff    in  Gegenwart katalytisch wirkender Metalle  oder Metallgemische,     Alkalimetalle    in Gegen  wart eines Alkohols oder Metalle und Säuren  zu nennen.  



  Das     Nipecotyl-tetrahydro-6-aethoxychino-          lin    bildet ein dickes Öl vom Siedepunkt     o,o2     185-186o, das in den meisten organischen       Lösungsmitteln    löslich ist. Mit Säuren werden  leicht lösliche, neutrale Salze erhalten.  



  Die neue Verbindung kann entweder  selbst therapeutische     Verwendung    finden oder  als Zwischenprodukt zur Herstellung phar  mazeutischer Verbindungen dienen.  



  <I>Beispiel:</I>  39,9 Teile     Nicotyl-tetrahydro-6-aethoxy-          chinolin    (erhalten durch Zusammenschmelzen  von     Nicotinsäurechlorid    mit Tetrahydro-6-         aethoxychinolin;    Schmelzpunkt 77-78o) wer  den mit 300 Teilen Alkohol und 15 Teilen     Nik-          kelkatalysator    unter 20-30 Atmosphären  Wasserstoffdruck auf 120-130o erhitzt.     Der-fil-          trierte        Autoklaveninhalt    wird vom Alkohol  befreit, und Rückstand im absoluten Vakuum  destilliert, wobei das     Nipecotyl-tetrahydro-6-          aethoxychinolin    rein erhalten wird.

    



  Die Hydrierung gelingt in gleicher Weise,  zum Beispiel bei Anwendung von Natrium  und Alkohol oder Zink in Gegenwart einer  Säure.



  Method for the preparation of an arm of a heteroyclic carboxylic acid. It has been found that an amide of a heterocyclic carboxylic acid can be obtained by hydrogenating the nicotyl-tetrahydro-6-ethoxyquinoline. Hydrogen in the presence of catalytically active metals or metal mixtures, alkali metals in the presence of an alcohol or metals and acids may be mentioned as hydrogenating agents.



  The nipecotyl-tetrahydro-6-ethoxyquinoline forms a thick oil with a boiling point of 0.02 185-186o, which is soluble in most organic solvents. Easily soluble, neutral salts are obtained with acids.



  The new compound can either find therapeutic use itself or serve as an intermediate for the preparation of pharmaceutical compounds.



  <I> Example: </I> 39.9 parts of nicotyl-tetrahydro-6-ethoxy-quinoline (obtained by melting nicotinic acid chloride with tetrahydro-6-ethoxyquinoline; melting point 77-78o) with 300 parts of alcohol and 15 parts of Nik - Freezing catalyst heated to 120-130o under 20-30 atmospheres of hydrogen pressure. The filtered contents of the autoclave are freed from alcohol and the residue is distilled in an absolute vacuum, the nipecotyl-tetrahydro-6-ethoxyquinoline being obtained in pure form.

    



  The hydrogenation succeeds in the same way, for example when using sodium and alcohol or zinc in the presence of an acid.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Amides einer heterocyclischen .Carbonsäure, dadurch gekennzeichnet, dass man das Nicotyl-tetra- hydro-6-aethoxychinolin hydriert. Das Nipecotyl-tetrahydro-6-aethoxychino- lin bildet ein dickes Öl vom Siedepunkt oo,2 18ä-186 , das in den meisten organischen Lösungsmitteln löslich ist. 'Mit Säuren wer den leicht lösliche, neutrale Salze erhalten. PATENT CLAIM: Process for the preparation of an amide of a heterocyclic .Carboxylic acid, characterized in that the nicotyl-tetrahydro-6-aethoxyquinoline is hydrogenated. Nipecotyl-tetrahydro-6-ethoxyquinoline forms a thick oil with a boiling point of 0.28-186, which is soluble in most organic solvents. 'With acids, easily soluble, neutral salts are obtained. Die neue Verbindung kann entweder selbst therapeutische Verwendung finden oder als Zwischenprodukt zur Herstellung phar mazeutischer Verbindungen dienen. UNTERANSYR CYCHE 1. Ausführungsform des Verfahrens nach Patentanspruch, dadurch gekennzeichnet, dass man die Hydrierung mit Wasserstoff in Gegenwart katalytisch wirkender Me talle ausübt. 2. Ausführungsform des Verfahrens nach Patentanspruch, dadurch gekennzeichnet, dass man die Hydrierung mit einem Alkali metall in Gegenwart eines Alkohols ausübt. 3. Ausführungsform des Verfahrens nach Patentanspruch, dadurch gekennzeichnet, dass man die Hydrierung mit einem reak tionsfähigen Metall in Gegenwart einer Säure ausübt. The new compound can either find therapeutic use itself or serve as an intermediate for the preparation of pharmaceutical compounds. UNTERANSYR CYCHE 1. embodiment of the process according to claim, characterized in that the hydrogenation is carried out with hydrogen in the presence of catalytically active metals. 2. Embodiment of the method according to claim, characterized in that the hydrogenation is carried out with an alkali metal in the presence of an alcohol. 3. Embodiment of the method according to claim, characterized in that the hydrogenation is carried out with a reactive metal in the presence of an acid.
CH142344D 1928-07-24 1928-07-24 Process for the preparation of an amide of a heterocyclic carboxylic acid. CH142344A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH142344T 1928-07-24
CH139805T 1928-07-24

Publications (1)

Publication Number Publication Date
CH142344A true CH142344A (en) 1930-09-15

Family

ID=25713400

Family Applications (1)

Application Number Title Priority Date Filing Date
CH142344D CH142344A (en) 1928-07-24 1928-07-24 Process for the preparation of an amide of a heterocyclic carboxylic acid.

Country Status (1)

Country Link
CH (1) CH142344A (en)

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