CH139805A - 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
CH139805A
CH139805A CH139805DA CH139805A CH 139805 A CH139805 A CH 139805A CH 139805D A CH139805D A CH 139805DA CH 139805 A CH139805 A CH 139805A
Authority
CH
Switzerland
Prior art keywords
preparation
hydrogenation
carboxylic acid
amide
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 CH139805A publication Critical patent/CH139805A/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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines     Armdes    einer     heterozyklisehen        Carbonsäure.       Es wurde     gefunclens    dass man zu einem       Amid    einer     heterozylD,lischen        Carbonsäure     gelangen kann, indem man den     NTicotyl-p-          aminobenzoesäureäthylester    hydriert. Als       Hydrierungsmittel    sind zum Beispiel Wasser  stoff in Gegenwart katalytisch wirkender  Metalle oder Metallgemische,     Alkalimetalle     in Gegenwart eines     Alkohols    oder Metalle  und Säuren zu nennen.  



  Der     Nipecotyl-p-aminobenzoesäureäthyl-          ester        .stellt    ein weisses Kristallpulver vom  Schmelzpunkt 160,5          dar. 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 pharma  zeutischer Verbindungen dienen.  



       BeisjxM:     59 Teile     I\Ticotyl-p-aminobenzoesä.ureäthyl-          esi:er    (erhalten aus     \ilzotinsäurechlorid    und         p-Aminobenzoesäureäthylester    bei Gegenwart  von     Pyridin;    filzige     Nädelchen    vom Schmelz  punkt<B>117</B>  ) werden mit 250 Teilen     Dekalin     und 15 Teilen     Nickelkataly        sator    unter 10 bis  40 Atmosphären Wasserstoffdruck auf 150  bis 165   erhitzt.

   Nach Beendigung der  Wasserstoffaufnahme wird das     Dekalin,    das  keine Substanz enthält, abgegossen, das zu  rückbleibende zähe Harz in heissem Aceton  gelöst und die Lösung vom Katalysator ab  filtriert. Beim Stehen scheidet sich der Ni  pecotyl-p-aminabenzoesäureester in schönen  Kristallen aus.  



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



  Method for preparing an arm of a heterocyclic carboxylic acid. It has been found that an amide of a heterocyclic carboxylic acid can be obtained by hydrogenating the ethyl Nicotyl-p-aminobenzoate. 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 ethyl nipecotyl-p-aminobenzoate is a white crystal powder with a melting point of 160.5 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.



       For example: 59 parts of ticotyl-p-aminobenzoesä.ureäthyl- esi: er (obtained from \ ilzotinic acid chloride and p-aminobenzoic acid ethyl ester in the presence of pyridine; felty needles with a melting point <B> 117 </B>) are mixed with 250 parts of decalin and 15 parts of nickel catalyst heated to 150 to 165 under 10 to 40 atmospheres of hydrogen pressure.

   After the uptake of hydrogen has ended, the decalin, which does not contain any substance, is poured off, the viscous resin that remains is dissolved in hot acetone and the solution is filtered off from the catalyst. When standing, the Ni pecotyl-p-aminabenzoic acid ester separates out in beautiful crystals.



  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 heterezyklischen Carbonsäure, da durch gekennzeichnet, dass man .den Nicotyl- p-aminobenzoesäureäthyles.ter hydriert. Der Nicotyl-p-aminobenzoesäureäthylester stellt ein weisses Kristallpulver vom Schmelz punkt 160,5 dar, dass in den meisten or ganischen Lösungsmitteln löslich ist. PATENT CLAIM: Process for the preparation of an amide of a heterocyclic carboxylic acid, characterized in that one hydrogenated the nicotyl-p-aminobenzoic acid ethyl ester. The ethyl nicotyl-p-aminobenzoate is a white crystal powder with a melting point of 160.5 that is soluble in most organic solvents. 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. UNTERANSPRüCHE 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 aus übt. 3. 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. SUBClaims 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. 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 a reactive metal in the presence of an acid.
CH139805D 1928-07-24 1928-07-24 Process for the preparation of an amide of a heterocyclic carboxylic acid. CH139805A (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
CH139805A true CH139805A (en) 1930-05-15

Family

ID=4396918

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139805D CH139805A (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) CH139805A (en)

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