CH142345A - 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
CH142345A
CH142345A CH142345DA CH142345A CH 142345 A CH142345 A CH 142345A CH 142345D A CH142345D A CH 142345DA CH 142345 A CH142345 A CH 142345A
Authority
CH
Switzerland
Prior art keywords
preparation
carboxylic acid
phenoxy
heterocyclic carboxylic
amide
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 CH142345A publication Critical patent/CH142345A/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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines     Amides    einer     heterocyelischen        Carbonsäure.       Es wurde gefunden, dass man zu einem       Amid    einer     lreterocyclischen        Carbonsäure    ge  langen kann, indem man das     Nicotyl-3',4'-          dimethoxy-3-phenoxy-4-methoxy-anilid    hy  driert.

   Als     Hydrierungsmittel    sind zum Bei  spiel     Wasserstoff    in Gegenwart katalytisch  wirkender     3letalle    oder     Metallgemische,    Al  kalimetalle in Gegenwart eines Alkohols oder  Metalle und     Säuren    zu nennen.  



  Das     Nipecotyl-3',4'-diinetlioxy-3-phenoxy-          4-tnethoxyanilid    stellt ein weisses Kristallpul  ver vom Schmelzpunkt<B>82--840</B> dar, das in  den meisten organischen Lösungsmitteln lös  lich 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>  18,3 Teile     Nlicot3#1-3',4'-dimethoxy-3-phe-          tioxy-4-uietliox3--anilid    werden mit 350 Tei-         len    Alkohol und 15 Teilen Nickelkatalysator  unter 20-30     At.        Wasserstoffdruck    auf       120--1251    erhitzt. Der filtrierte     Autoklaven-          inhalt    wird konzentriert, wobei das     Nipecotyl-          3',4'-dimetboxy-3-phenoxy-4-methoxy-anilid     auskristallisiert.

   Zur Herstellung des     Nicotyl-          3',4'-ditnethoxy-3-phenoxy    - 4-     methoxy-anilids     vom Schmelzpunkt 164-167   geht man  folgendermassen vor:     Nitroguajacolkalium    wird  mit     Bromveratrol    bei Gegenwart von Kupfer  umgesetzt. Das so erhaltene     3',4'-Dimethoxy-3-          phenoxy-4-methoxy-nitrobenzol    vom Schmelz  punkt 108-109   wird mit Eisen und Salz  säure zur     Aminoverbindung    (Schmelzpunkt       135-136")    reduziert und diese mit     Nicotin-          säurechlorid    umgesetzt.  



  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 carboxylic acid. It has been found that an amide of a heterocyclic carboxylic acid can be obtained by hydrogenating nicotyl-3 ', 4'-dimethoxy-3-phenoxy-4-methoxy-anilide.

   Hydrogenating agents which may be mentioned are, for example, hydrogen in the presence of catalytically active metals or metal mixtures, alkali metals in the presence of an alcohol or metals and acids.



  Nipecotyl-3 ', 4'-diinetlioxy-3-phenoxy-4-methoxyanilide is a white crystal powder with a melting point of <B> 82-840 </B> 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> 18.3 parts of Nlicot3 # 1-3 ', 4'-dimethoxy-3-phe- tioxy-4-uietliox3 - anilide are mixed with 350 parts of alcohol and 15 parts of nickel catalyst under 20 -30 at. Hydrogen pressure heated to 120-1251. The filtered contents of the autoclave are concentrated, the nipecotyl-3 ', 4'-dimetboxy-3-phenoxy-4-methoxy-anilide crystallizing out.

   To prepare nicotyl-3 ', 4'-ditnethoxy-3-phenoxy-4-methoxy-anilide with a melting point of 164-167, the following procedure is followed: Nitroguaiacol potassium is reacted with bromeveratrole in the presence of copper. The 3 ', 4'-dimethoxy-3-phenoxy-4-methoxy-nitrobenzene obtained in this way, having a melting point of 108-109, is reduced to the amino compound (melting point 135-136 ") with iron and hydrochloric acid and this is reacted with nicotinic acid chloride.



  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 Armdes einer heterocyclischen Carbonsäure, dadurch gekennzeichnet, dass man das Nicotyl-3'-4'-di- methoxy-3-phenoxy-4-inethoxy-anilid hydriert. Das Nipecotyl-3',4'-dimetlioxy-3-phenoxy- 4-metlioxyanilid stellt ein weisses Kristall pulver vom Schmelzpunkt 82-84 dar, das in den meisten organischen Lösungsmitteln löslich ist. Mit Säuren werden leicht lösliche, neutrale Salze erhalten. Claim: Process for the preparation of an arm of a heterocyclic carboxylic acid, characterized in that nicotyl-3'-4'-dimethoxy-3-phenoxy-4-ynethoxy-anilide is hydrogenated. The nipecotyl-3 ', 4'-dimetlioxy-3-phenoxy-4-metlioxyanilid is a white crystal powder with a melting point of 82-84, which is soluble in most organic solvents. Easily soluble, neutral salts are obtained with acids. Die neue Verbindung kann entweder selbst therapeutische Verwendung finden oder als Zwischenprodukt zur Herstellung pharma zeutischer Verbindungen dienen. UNTERANSPRtrCHE 1. Ausführungsform. des Verfahrens nach Pa tentanspruch, dadurch gekennzeichnet, dass man die Hydrierung mit Wasserstoff in Gegenwart katalytisch wirkender Metalle ausübt. 2. The new compound can either find therapeutic use itself or serve as an intermediate for the preparation of pharmaceutical compounds. SUBClaims 1st embodiment. of the process according to patent claim, characterized in that the hydrogenation is carried out with hydrogen in the presence of catalytically active metals. 2. Ausführungsform des Verfahrens nach Pa tentanspruch, dadurch gekennzeichnet, dass man die IIy drierung mit einem Alkaliine- tall in Gegenwart eines Alkohols ausübt. 3. Ausführungsform des Verfahrens nach Pa tentanspruch, dadureli gekennzeichnet, dass man die. Hydrierung mit eineue reaktions fähigen Metall in Gegenwart einer Säure ausübt. Embodiment of the method according to patent claim, characterized in that the IIy dration is carried out with an alkali metal in the presence of an alcohol. 3. Embodiment of the method according to Pa tentansruf, dadureli characterized in that one the. Carries out hydrogenation with a reactive metal in the presence of an acid.
CH142345D 1928-07-24 1928-07-24 Process for the preparation of an amide of a heterocyclic carboxylic acid. CH142345A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139805T 1928-07-24
CH142345T 1928-07-24

Publications (1)

Publication Number Publication Date
CH142345A true CH142345A (en) 1930-09-15

Family

ID=25713401

Family Applications (1)

Application Number Title Priority Date Filing Date
CH142345D CH142345A (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) CH142345A (en)

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