CH192778A - Process for the preparation of a substituted pyridine-o-dicarboxamide. - Google Patents

Process for the preparation of a substituted pyridine-o-dicarboxamide.

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Publication number
CH192778A
CH192778A CH192778DA CH192778A CH 192778 A CH192778 A CH 192778A CH 192778D A CH192778D A CH 192778DA CH 192778 A CH192778 A CH 192778A
Authority
CH
Switzerland
Prior art keywords
reaction
pyridine
dicarboxylic acid
carried out
propylamine
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 CH192778A publication Critical patent/CH192778A/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

Landscapes

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

Description

  

  Verfahren zur Herstellung eines substituierten     Pyridin-o-diearbonsäureamides.       Es wurde gefunden, dass man zu einem  substituierten     Pyridin-o-dicarbon.säureamid     gelangen kann, wenn man auf eine Verbin  dung, die das Radikal der Formel  
EMI0001.0003     
    enthält, wie z. B. die     Pyridin-3.        4-dicarbon-          säure,    ihre     Halogenide,    Ester, Salze oder ihr       Anhydrid,        Di-n-propylamin    einwirken lässt.  



  Das so gewonnene     Pyridin-3.        4-dicarbon-          säure-biss-(di-n-propylamid)    ist ein gelbliches       Ö1,    das bei 180   C unter 0,3 mm Druck       siedet    und in vielen organischen     Lösungsmit-          teln    leicht löslich ist.  



  Bei obiger Reaktion lassen sich     Konden-          eationsmittel    wie     Phosphorhalogenide,        Thio-          nylchlorid,        Phosgen    oder     Phosphorpentogyd,     insbesondere bei der Umsetzung der freien         Pyridin-3.4-dicarbonsäure    mit     Di-n-propyl-          amin,    verwenden.  



  Die neue Verbindung hat     eine        günstig"     Wirkung auf Kreislauf und Atmung. Sie  soll therapeutische Verwendung finden.  



       Beispiel:     20 Teile     Pyridin-3.4-diearbonsäuredi-          chlorid    (erhalten durch Erhitzen von     Pyri-          din-3.4-dicarboneäure    und     Phosphorpenta-          chlorid)    werden in ätherischer Lösung mit  25 Teilen     Di-n-propylamin        in.    Gegenwart von  27 Teilen 30%iger Natronlauge unter Küh  lung umgesetzt.

   Man fügt Natronlauge zu,  trennt die ätherische Lösung ab, trocknet sie  und vertreibt das Lösungsmittel :sowie freies       Di-n-propylamin.        Das,    zurückbleibende     Py-          ridin    - 3. 4 -     diearbonsäure-bis-        (di-n-propyl-          amid)        kann        durch    Destillation gereinigt wer  den.  



  Dieselbe     Verbindung    wird auch erhal  ten, wenn man     Pyridin-3        .4-diaarbonsäure-          dichlorid    oder ein     anderes.        Halogenid        mit         einem Überschuss von     Di-n-propylamin    ohne  Zusatz von Alkali umsetzt oder wenn man  es mit     Di-n-propylamin-hydrochlorid,    aus  dem sich während der Umsetzung     Di-n-pro-          pylamin    bildet, auf 120 bis<B>160'</B> erwärmt.

         Pyridin-    3 .     4-,dicarbonsäure-bis-(di-n-propyl-          amid)    kann ferner durch Umsetzung von     Py-          ridin-3.4-dicarbonsäure    mit     Di-n-propyl-          amin    in Gegenwart von     Phosphoroxychlorid     oder einem andern Kondensationsmittel wie  z.

   B.     Phosphorpentoxyd    oder     Thionylchlorid     erhalten werden.     Dasselbe    Endprodukt ge  winnt man durch     Einwirkung    von     Di-n-pro-          pylamin    auf     Pyridin-3.4-dicarbonsäurean-          hydrid    unter Zusatz eines     Kondensations-          mittels.    wie z. B.     Phosphoroxyehlorid.  



  Process for the preparation of a substituted pyridine-o-diacid amide. It has been found that a substituted pyridine-o-dicarbon.säureamid can be obtained if one uses a compound which contains the radical of the formula
EMI0001.0003
    contains, such as B. the pyridine-3. 4-dicarboxylic acid, its halides, esters, salts or its anhydride, di-n-propylamine, can act.



  The thus obtained pyridine-3. 4-dicarboxylic acid biss- (di-n-propylamide) is a yellowish oil that boils at 180 C under 0.3 mm pressure and is easily soluble in many organic solvents.



  In the above reaction, condensation agents such as phosphorus halides, thionyl chloride, phosgene or phosphorus pentogide can be used, in particular in the reaction of the free pyridine-3,4-dicarboxylic acid with di-n-propylamine.



  The new compound has a beneficial effect on the circulatory system and respiration. It is said to be of therapeutic use.



       Example: 20 parts of pyridine-3,4-dicarboxylic acid dichloride (obtained by heating pyridine-3,4-dicarboxylic acid and phosphorus pentachloride) in an ethereal solution with 25 parts of di-n-propylamine in the presence of 27 parts of 30% sodium hydroxide solution implemented under cooling.

   Sodium hydroxide is added, the ethereal solution is separated off, it is dried and the solvent is driven off: as well as free di-n-propylamine. The remaining pyridine - 3. 4 - diarboxylic acid bis (di-n-propyl amide) can be purified by distillation.



  The same compound is also obtained if one uses pyridine-3 .4-diaarboxylic acid dichloride or another. Halide is reacted with an excess of di-n-propylamine without the addition of alkali or if it is reacted with di-n-propylamine hydrochloride, from which di-n-propylamine is formed during the reaction, to 120 to 160 '</B> heated.

         Pyridine- 3. 4-, dicarboxylic acid bis (di-n-propyl amide) can also be obtained by reacting pyridine-3,4-dicarboxylic acid with di-n-propyl amine in the presence of phosphorus oxychloride or another condensing agent such as.

   B. phosphorus pentoxide or thionyl chloride can be obtained. The same end product is obtained by the action of di-n-propylamine on pyridine-3,4-dicarboxylic anhydride with the addition of a condensation agent. such as B. phosphorus oxychloride.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines substi- tuierten Pyridin-o-dicarbonsäureamidee, da durch gekennzeichnet, dass man auf eine Ver bindung, die .das Radikal der Formel EMI0002.0028 enthält, Di-n-propylamin einwirken lässt. PATENT CLAIM: Process for the preparation of a substituted pyridine-o-dicarboxamide, characterized in that one is linked to a compound that has the .the radical of the formula EMI0002.0028 contains, allows di-n-propylamine to act. Das so gewonnene Pyridin-3. 4-dicarbon- säure-bis-(di-n-propylamid) ist ein gelbliches 01, das bei<B>1.80'</B> C unter 0,3 mm Druck siedet und in vielen organischen Löeungsmit- teln leicht löslich ist. Die neue Verbindung hat eine günstige Wirkung auf Kreislauf und Atmung. Sie soll therapeutische Verwendung finden. UI\TTERANSPRMHE 1. The thus obtained pyridine-3. 4-dicarboxylic acid bis (di-n-propylamide) is a yellowish oil that boils at <B> 1.80 '</B> C under 0.3 mm pressure and is easily soluble in many organic solvents. The new compound has a beneficial effect on circulation and breathing. It should find therapeutic use. UI \ TTERPRMHE 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung .ein Halogenid der Pyridin-3. 4-dicarbon- säure verwendet. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung einen Ester der Pyridin-3.4-dicarbon- säure verwendet. 3. Verfahren nach Patsntanspruch,dadurch gekennzeichnet, dass man zur Umsetzung Pyridin-3.4-dicarbonsäureanhydrid ver wendet. 4. Process according to patent claim, characterized in that a halide of pyridine-3. 4-dicarboxylic acid is used. 2. The method according to claim, characterized in that an ester of pyridine-3,4-dicarboxylic acid is used for the reaction. 3. The method according to patent claim, characterized in that pyridine-3,4-dicarboxylic anhydride is used for the reaction. 4th Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung Pyridin-2. 3-dicarbonsäure verwendet. 5. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung ein Salz der Pyridin 3. 4-dicarbonsäure verwendet. 6. Verfahren nach Patentanspruch, dadurch gekennzeichnet, .dass man zur Umsetzung Di-n-propylamin verwendet, das aus einem Salz des Di-n-propylamins erhal ten wurde. 7. Process according to patent claim, characterized in that pyridine-2. 3-dicarboxylic acid used. 5. The method according to claim, characterized in that a salt of pyridine 3. 4-dicarboxylic acid is used for the reaction. 6. The method according to claim, characterized in that .dass using di-n-propylamine for the reaction, which was obtained from a salt of di-n-propylamine. 7th Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Reaktion in Gegenwart eines Kondensationsmittels ausführt. B. Verfahren nach Patentanspruch und Un teranspruch 7, dadurch gekennzeichnet, dass man die Reaktion in Gegenwart eines Phosphorhalogenids ausführt. 9. Verfahren nach Patentanspruch und Un teranspruch 7, dadurch gekennzeichnet, dass man die Reaktion in Gegenwart von Phosphoroxychlorid ausführt. 10. Process according to patent claim, characterized in that the reaction is carried out in the presence of a condensing agent. B. The method according to patent claim and un teran claim 7, characterized in that the reaction is carried out in the presence of a phosphorus halide. 9. The method according to patent claim and un teran claim 7, characterized in that the reaction is carried out in the presence of phosphorus oxychloride. 10. Verfahren nach Patentanspruch und Un teranspruch 7, dadurch gekennzeichnet, dass man die Reaktion in Gegenwart von Thionylchlorid ausführt. 11. Verfahren nach Patentanspruch und Un teranspruch 7, dadurch gekennzeichnet, dass man die Reaktion in Gegenwart von Phosgen ausführt. 12. Verfahren nach Patentanspruch und Un teranspruch 7, dadurch gekennzeichnet, .dass man die Reaktion in Gegenwart von Phosphorpentoxyd ausführt. Process according to patent claim and un teran claim 7, characterized in that the reaction is carried out in the presence of thionyl chloride. 11. The method according to patent claim and un teran claim 7, characterized in that the reaction is carried out in the presence of phosgene. 12. The method according to claim and sub-claim 7, characterized in that the reaction is carried out in the presence of phosphorus pentoxide.
CH192778D 1934-12-05 1934-12-05 Process for the preparation of a substituted pyridine-o-dicarboxamide. CH192778A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH192778T 1934-12-05
CH188152T 1934-12-05

Publications (1)

Publication Number Publication Date
CH192778A true CH192778A (en) 1937-08-31

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Family Applications (1)

Application Number Title Priority Date Filing Date
CH192778D CH192778A (en) 1934-12-05 1934-12-05 Process for the preparation of a substituted pyridine-o-dicarboxamide.

Country Status (1)

Country Link
CH (1) CH192778A (en)

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