CH150126A - Process for the preparation of an N-substituted compound of the pyridone series. - Google Patents

Process for the preparation of an N-substituted compound of the pyridone series.

Info

Publication number
CH150126A
CH150126A CH150126DA CH150126A CH 150126 A CH150126 A CH 150126A CH 150126D A CH150126D A CH 150126DA CH 150126 A CH150126 A CH 150126A
Authority
CH
Switzerland
Prior art keywords
preparation
pyridone
substituted compound
water
melts
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 CH150126A publication Critical patent/CH150126A/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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6

Description

  

  Verfahren zur Darstellung einer     N-substituierten    Verbindung der     Pyridonreihe.       Es wurde gefunden, dass man zu einer       N-substituierten    Verbindung der     Pyridonreihe     gelangen kann, wenn man einen Ester des       Diäthylaminoäthanols    an     Pyridin    anlagert und  das Additionsprodukt oxydiert.  



  Das entstandene     N-Diäthylaminoäthyl-2-          pyridon    siedet bei 127   unter 1 mm Druck.  Es ist in Wasser und in organischen Lösungs  mitteln, sowie in Säuren löslich. Das farblose       Monochlorhydrat    kristallisiert mit 1     Mol    Was  ser und schmilzt bei 740. Wasserfrei schmilzt  es bei 148  .  



  Die neue Base soll für therapeutische  Zwecke Verwendung finden.  



  <I>Beispiel:</I>  Äquivalente Mengen     Pyridin    und Chlor  äthyldiäthylaminchlorhydrat werden einige  Zeit auf etwa 125   erhitzt. 50,2 Teile des  Reaktionsproduktes werden in Wasser gelöst  und nach Zusatz von 32 Teilen     Natriumhy-          droxyd    in der gälte mit einer wässerigen  Lösung von 130 Teilen     galirimferricyanid       versetzt. Nach erfolgter Oxydation wird das       N-Diäthylaminoäthyl-2-pyridon    mit Benzol  ausgezogen und hierauf das Lösungsmittel  vertrieben.  



  Durch Destillation erhält     inan    die Base  in reiner Form.  



  Für die Anlagerung au     Pyridin    können  an Stelle des     Chlorides    auch andere Ester  des     Diäthylamirioäthanols,    z. B. das     Bromid     oder aromatische     Sulfosäureester,    Verwendung  finden. Ferner lässt sich die Oxydation der       quaternären    Base auch auf andere Weise,  z. B. auf elektrolytischem Wege, durchführen.



  Process for the preparation of an N-substituted compound of the pyridone series. It has been found that an N-substituted compound of the pyridone series can be obtained if an ester of diethylaminoethanol is added to pyridine and the addition product is oxidized.



  The resulting N-diethylaminoethyl-2-pyridone boils at 127 under 1 mm pressure. It is soluble in water and in organic solvents as well as in acids. The colorless monochlorohydrate crystallizes with 1 mol of water and melts at 740. Anhydrous, it melts at 148.



  The new base will be used for therapeutic purposes.



  <I> Example: </I> Equivalent amounts of pyridine and chlorine ethyl diethylamine chlorohydrate are heated to about 125 for some time. 50.2 parts of the reaction product are dissolved in water and, after 32 parts of sodium hydroxide have been added, an aqueous solution of 130 parts of galimferricyanide is added. After oxidation has taken place, the N-diethylaminoethyl-2-pyridone is extracted with benzene and the solvent is then driven off.



  The base is obtained in pure form by distillation.



  For the addition of pyridine, other esters of diethylamine ethanol, e.g. B. the bromide or aromatic sulfonic acid ester, use. Furthermore, the oxidation of the quaternary base can also be done in other ways, e.g. B. electrolytically perform.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung einer N-substi- tuierten Verbindung der Pyridonreihe, da durch gekennzeichnet, dass man einen Ester des Diäthylamitioäthanols an Pyridin anlagert und das Additionsprodukt oxydiert. Das entstandene N-Diäthylaminoäthyl-2- pyridon siedet bei 127 unter 1 rnni Druck. Es ist in Wasser und in organischen Lösungs- mitteln, sowie in Säuren löslich. PATENT CLAIM: Process for the preparation of an N-substituted compound of the pyridone series, characterized in that an ester of diethylamitioethanol is added to pyridine and the addition product is oxidized. The resulting N-diethylaminoethyl-2-pyridone boils at 127 under 1 mm pressure. It is soluble in water and organic solvents as well as acids. Das farblose Monochlorhydrat kristallisiert mit 1 Mol Was ser und schmilzt bei 74 . Wasserfrei schmilzt es bei 148 . Die neue Base soll für therapeutische Zwecke Verwendung -finden. The colorless monochlorohydrate crystallizes with 1 mol of water and melts at 74. Anhydrous it melts at 148. The new base is intended to be used for therapeutic purposes.
CH150126D 1929-08-10 1929-08-10 Process for the preparation of an N-substituted compound of the pyridone series. CH150126A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH150126T 1929-08-10

Publications (1)

Publication Number Publication Date
CH150126A true CH150126A (en) 1931-10-15

Family

ID=4405576

Family Applications (1)

Application Number Title Priority Date Filing Date
CH150126D CH150126A (en) 1929-08-10 1929-08-10 Process for the preparation of an N-substituted compound of the pyridone series.

Country Status (1)

Country Link
CH (1) CH150126A (en)

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