CH142343A - 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.

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Publication number
CH142343A
CH142343A CH142343DA CH142343A CH 142343 A CH142343 A CH 142343A CH 142343D A CH142343D A CH 142343DA CH 142343 A CH142343 A CH 142343A
Authority
CH
Switzerland
Prior art keywords
preparation
amide
hydrogenation
carboxylic acid
carried out
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 CH142343A publication Critical patent/CH142343A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

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

Description

  

  verfahren zur Darstellung eines     Amides    einer     heterocyelischen        Carl)onsäure.       Es wurde gefunden, dass man zu einem       Amid    einer     heterocyclischen        Carbousäure    ge  langen kann; indem man das     Nicotyl-ac-tetra-          hydro-R-naphtylamid    hydriert. Als     Hydrie-          rungsmittel    sind     zucn    Beispiel Wasserstoff  in Gegenwart katalytisch wirkender Metalle  oder Metallgemische,     Alkalimetalle    in Gegen  wart eines Alkohols oder Metalle und Säuren  zu nennen.  



  Das     Nipecotyl-ac-tetrah3-dro-@-naphtylamid     stellt ein weisses     Kristallpulver    vom Schmelz  punkt 132   dar, das in den meisten orga  nischen 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 pharmazeu  tischer Verbindungen dienen.    <I>Beispiel:</I>    59,1 Teile     Nicotyl-ac-tetrahydro-@-naphtyl-          amid    (erhalten durch Zusammenschmelzen  von     Nicotinsäurechlorid    und     ac-Tetrahydro-          13-naphtylamin-chlorhydrat;    Schmelzpunkt         137-188")    werden mit 210 Teilen     Dekalin     und 15 Teilen Nickelkatalysator unter 20-40  Atmosphären Wasserstoffdruck auf 140-150   erhitzt.

   Nach Beendigung der Wasserstoff  aufnahme wird der     Autoklaveninhalt    mit Al  kohol verdünnt und filtriert. Das Filtrat wird  vom Lösungsmittel befreit und der Rück  stand mit etwas Äther ausgewaschen. Das  fast in quantitativer Ausbeute     zurückbleibende     weisse Pulver ist reines     Nipecotyl-ac:        tetra-          hydro-ss-naphtylamid.     



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



  process for the preparation of an amide of a heterocyclic carl) onic acid. It has been found that an amide of a heterocyclic carbous acid can be obtained; by hydrogenating the nicotyl-ac-tetra-hydro-R-naphthylamide. Examples of hydrogenating agents are hydrogen in the presence of catalytically active metals or metal mixtures, alkali metals in the presence of an alcohol or metals and acids.



  The nipecotyl-ac-tetrah3-dro - @ - naphthylamide is a white crystal powder with a melting point of 132 that 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> 59.1 parts of nicotyl-ac-tetrahydro - @ - naphthyl amide (obtained by melting nicotinic acid chloride and ac-tetrahydro-13-naphthylamine chlorohydrate; melting point 137-188 ") with 210 Parts of decalin and 15 parts of nickel catalyst heated to 140-150 under 20-40 atmospheres of hydrogen pressure.

   After the hydrogen uptake has ended, the contents of the autoclave are diluted with alcohol and filtered. The filtrate is freed from the solvent and the residue was washed out with a little ether. The white powder that remains almost in quantitative yield is pure nipecotyl-ac: tetra-hydro-ss-naphthylamide.



  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-ac- tetrahydro-p-naphtylamid hydriert. Das N ipecotyl-ac-tetrahydro-ss-naphtylaniid stellt ein weisses Kristallpulver vorn Schmelz punkt 132 dar, das in den meisten organi- sehen 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 pharma zeutischer Verbindungen dienen. UNTERANSPRt1CHE 1. PATENT CLAIM: A process for the preparation of an amide of a heterocyclic carboxylic acid, characterized in that the nicotyl-ac- tetrahydro-p-naphthylamide is hydrogenated. The nipecotyl-ac-tetrahydro-ss-naphthylaniid is a white crystal powder with a melting point of 132 that 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. SUB-CLAIM 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 Al kalimetall 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. 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; 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.
CH142343D 1928-07-24 1928-07-24 Process for the preparation of an amide of a heterocyclic carboxylic acid. CH142343A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH142343T 1928-07-24
CH139805T 1928-07-24

Publications (1)

Publication Number Publication Date
CH142343A true CH142343A (en) 1930-09-15

Family

ID=25713399

Family Applications (1)

Application Number Title Priority Date Filing Date
CH142343D CH142343A (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) CH142343A (en)

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