CH151888A - 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.

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Publication number
CH151888A
CH151888A CH151888DA CH151888A CH 151888 A CH151888 A CH 151888A CH 151888D A CH151888D A CH 151888DA CH 151888 A CH151888 A CH 151888A
Authority
CH
Switzerland
Prior art keywords
preparation
substituted compound
pyridone series
pyridone
series
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 CH151888A publication Critical patent/CH151888A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C07D217/24—Oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

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



  Das entstandene N -     Diäthylaminoäthyl-          isochinolon    ist ein gelbes Öl; es siedet bei  175--17$" unter 1,5 mm Druck. Es ist un  löslich in     Wasser,''gut    löslich in organischen  Lösungsmitteln, sowie in Säuren. Das     Pikrat     schmilzt bei     162-1641'.     



  Die neue Base soll für therapeutische  Zwecke Verwendung finden.    <I>Beispiel:</I>  Äquivalente Mengen     Isochinolin    und     Chlor-          äthyldiäthylaminchlorhydrat    werden auf 125    erhitzt, bis das Reaktionsprodukt wasserlös  lich ist.

   30 Teile des so erhaltenen     Diäthyl-          aminoisochinoliniumohlorides    werden in Was  ser gelöst und nach Zusatz von 30 Teilen       Kaliumhydroxyd    mit einer     wässerigen    Lösung    von 66 Teilen     Kaliumferricyanid    versetzt  Nach erfolgter Oxydation wird das gebildete       galiumferrocyanid        abfiltriert    und die Base  durch Zugabe von Alkali als Öl vollständig  abgeschieden.

   Durch Destillation erhält man  das     N-Diäthylaminoäthylisochinolon    in reiner  Form:  Für die Anlagerung an     Isochinolin    kön  nen an Stelle des     Chlorides    auch andere  Ester des     Diäthylaminoäthanols,    zum Beispiel  das     Bromid    oder aromatische     Sulfosäureester,     Verwendung finden. Ferner lässt sich die  Oxydation der     quaternären    Base auch auf  andere Weise, zum Beispiel auf elektrolyti  schem Wege, durchführen.



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



  The resulting N - diethylaminoethyl isoquinolone is a yellow oil; it boils at $ 175--17 "under 1.5 mm pressure. It is insoluble in water," readily soluble in organic solvents and acids. The picrate melts at 162-1641 '.



  The new base will be used for therapeutic purposes. <I> Example: </I> Equivalent amounts of isoquinoline and chloroethyl diethylamine chlorohydrate are heated to 125 until the reaction product is water-soluble.

   30 parts of the diethyl aminoisoquinolinium chloride obtained in this way are dissolved in what water and, after the addition of 30 parts of potassium hydroxide, an aqueous solution of 66 parts of potassium ferricyanide is added.

   The N-diethylaminoethylisoquinolone is obtained in pure form by distillation: for the addition to isoquinoline, other diethylaminoethanol esters, for example bromide or aromatic sulfonic acid esters, can be used instead of the chloride. Furthermore, the oxidation of the quaternary base can also be carried out in other ways, for example in an electrolytic way.

Claims (1)

PATENTANSPRUCH Verfahren zur Darstellung einer N-substi- tuierten Verbindung der Pyridonreihe, dadurch gekennzeichnet, dass man einen Ester des Diäthylaminoäthanols an Isochinolin anlagert und das Additionsprodukt oxydiert. Das entstandene N - Diäthylaminoäthyl- isochinolon ist ein gelbes Öl ; es siedet bei 175-178 unter 1,5 mm Druck. Es ist un löslich in Wasser, gut löslich in organischen Lösungsmitteln, sowie in Säuren. PATENT CLAIM Process for the preparation of an N-substituted compound of the pyridone series, characterized in that an ester of diethylaminoethanol is added to isoquinoline and the addition product is oxidized. The resulting N - diethylaminoethyl isoquinolone is a yellow oil; it boils at 175-178 under 1.5mm pressure. It is insoluble in water, readily soluble in organic solvents and acids. Das Pikrat schmilzt bei 162-1640. Die neue Base soll für therapeutische Zwecke Verwendung finden. The picrate melts at 162-1640. The new base will be used for therapeutic purposes.
CH151888D 1929-08-10 1929-08-10 Process for the preparation of an N-substituted compound of the pyridone series. CH151888A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH150126T 1929-08-10
CH151888T 1929-08-10

Publications (1)

Publication Number Publication Date
CH151888A true CH151888A (en) 1931-12-31

Family

ID=25715579

Family Applications (1)

Application Number Title Priority Date Filing Date
CH151888D CH151888A (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) CH151888A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2593798A (en) * 1947-05-22 1952-04-22 Searle & Co Aminoalkylamino isoquinoline compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2593798A (en) * 1947-05-22 1952-04-22 Searle & Co Aminoalkylamino isoquinoline compounds

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