CH150127A - 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
CH150127A
CH150127A CH150127DA CH150127A CH 150127 A CH150127 A CH 150127A CH 150127D A CH150127D A CH 150127DA CH 150127 A CH150127 A CH 150127A
Authority
CH
Switzerland
Prior art keywords
pyridone
preparation
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 CH150127A publication Critical patent/CH150127A/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-snbstituierten    Verbindung der     Pyridonreilie.       Es wurde gefunden, dass man zu einer       N-substituierten    Verbindung der     Pyridonreihe     gelangen kann, wenn man     2-Pyridon    mit  einem Ester des     Diäthylaminoäthanols    in  Gegenwart säurebindender Mittel umsetzt.  



  Das entstandene     N-Diäthylaminoaethyl-3-          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     Wasser und schmilzt bei     7411.    Wasserfrei  schmilzt es bei 148  .  



  Die neue Base soll für therapeutische  Zwecke Verwendung finden.  



       Beispiel          Man    gibt 38 Teile     2-Pyridon    zu einer  alkoholischen Lösung von 9,2 Teilen Natrium.  Hierauf destilliert man den Alkohol ab und  erhitzt nach Zusatz von     Toluol    mit 70 Teilen       Chloräthyldiäthylamin.    Nach beendeter Reak  tion wird das Lösungsmittel abgetrieben und  der Rückstand vom gleichzeitig gebildeten,    niedriger siedenden     2-Diäthylaminoäthoxy-          pyridin    getrennt. Dies geschieht entweder  durch     Wasserdampfdestillation,    wobei der  Äther allein überdestilliert, oder durch Frak  tionierung.  



  Die Fraktion von<B>120-1301</B> unter 1 mm  Druck wird gesondert aufgefangen und durch  nochmalige Destillation gereinigt.  



  Als säurebindende Mittel können zum  Beispiel auch     Alkalihydrogyde    oder     -carbonate     Verwendung finden. Ebenso lässt sich das       Toluol    durch andere Lösungsmittel, zum Bei  spiel durch     Älkokol,    Aceton, Wasser usw.,  ersetzen.  



  An Stelle des     Chlorides    können auch  andere Ester des     Diäthylaminoäthaiiols.    zum  Beispiel das     Bromid    oder aromatische     Sulfo-          säureester,    Verwendung     finden.  



  Process for the preparation of an N-substituted compound of the pyridone line. It has been found that an N-substituted compound of the pyridone series can be obtained if 2-pyridone is reacted with an ester of diethylaminoethanol in the presence of acid-binding agents.



  The resulting N-diethylaminoethyl-3-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 7411. Anhydrous, it melts at 148.



  The new base will be used for therapeutic purposes.



       Example 38 parts of 2-pyridone are added to an alcoholic solution of 9.2 parts of sodium. The alcohol is then distilled off and, after the addition of toluene, heated with 70 parts of chloroethyl diethylamine. After the reaction has ended, the solvent is driven off and the residue is separated from the lower-boiling 2-diethylaminoethoxypyridine which is formed at the same time. This is done either by steam distillation, with the ether distilling over by itself, or by fractionation.



  The fraction of <B> 120-1301 </B> under 1 mm pressure is collected separately and purified by repeated distillation.



  Alkali hydroxides or carbonates, for example, can also be used as acid-binding agents. Likewise, the toluene can be replaced by other solvents, for example with Älkokol, acetone, water, etc.



  Other esters of diethylaminoethaiiol can also be used in place of the chloride. for example the bromide or aromatic sulfonic acid esters can be used.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung einer N-substi- tuierten Verbindung der Pyridanreilie, da durch gekennzeichnet, da13 man 2-Pyridon mit einem Ester des Diäthylaminoäthanols in Gegenwart säurebindender Mittel umsetzt. Das entstandene N-Diäthylaminoäthyl-2- pyridon siedet bei<B>127'</B> unter 1 mm Druck. Es ist in Wasser und in organischen Lösungs mitteln, sowie in -Säuren löslich. Das farb lose Monochlorhydrat kristallisiert mit 1 AIol Wasser und schmilzt bei 74 . Wasserfrei schmilzt es bei 148'. PATENT CLAIM: Process for the preparation of an N-substituted compound of the pyridane series, characterized in that 2-pyridone is reacted with an ester of diethylaminoethanol in the presence of acid-binding agents. The resulting N-diethylaminoethyl-2-pyridone boils at <B> 127 '</B> under 1 mm pressure. It is soluble in water and in organic solvents as well as in acids. The colorless monochlorohydrate crystallizes with 1 alcohol of water and melts at 74. Anhydrous it melts at 148 '. Die neue Base soll für therapeutische Zwecke Verwendung finden. The new base will be used for therapeutic purposes.
CH150127D 1929-08-10 1929-08-10 Process for the preparation of an N-substituted compound of the pyridone series. CH150127A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH150127T 1929-08-10

Publications (1)

Publication Number Publication Date
CH150127A true CH150127A (en) 1931-10-15

Family

ID=4405578

Family Applications (1)

Application Number Title Priority Date Filing Date
CH150127D CH150127A (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) CH150127A (en)

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