CH155447A - Process for the preparation of 4-oxypyridine. - Google Patents

Process for the preparation of 4-oxypyridine.

Info

Publication number
CH155447A
CH155447A CH155447DA CH155447A CH 155447 A CH155447 A CH 155447A CH 155447D A CH155447D A CH 155447DA CH 155447 A CH155447 A CH 155447A
Authority
CH
Switzerland
Prior art keywords
preparation
oxypyridine
pyridyl
evaporated
aminopyridine
Prior art date
Application number
Other languages
German (de)
Inventor
Ernst Dr Koenigs
Greiner Heinz
Original Assignee
Ernst Dr Koenigs
Greiner Heinz
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 Ernst Dr Koenigs, Greiner Heinz filed Critical Ernst Dr Koenigs
Publication of CH155447A publication Critical patent/CH155447A/en

Links

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
    • C07D213/68—One oxygen atom attached in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Description

  

  Verfahren zur Darstellung von     4-Ogypyridin.       Durch das Schweiz. Hauptpatent     Nr.150299     wird ein Verfahren zur Darstellung von     4-          Aminopyridin    geschützt, das dadurch gekenn  zeichnet ist, dass man     Pyridin    durch Einwir  ken von     Thioylchlorid    zu     4-Pyridyl-Pyridinium-          dichlorid    umsetzt und dieses durch Behand  lung mit alkalisch wirkenden Mitteln in 4  Aminopyridin umwandelt.  



  Bei der weitem Bearbeitung wurde nun  gefunden, dass     4-Pyridyl-pyridiniumdichlorid     nicht nur ein geeignetes Ausgangsmaterial  für die Darstellung des     4-Aminopyridins    ist,  sondern sich auch durch Einwirken     hydrogyl-          haltiger    Substanzen in andere, in     4-Stellung     substituierte     Pyridine    umwandeln lässt.  



  Gegenstand vorliegender Erfindung ist  nun ein Verfahren zur Darstellung von -4  Ogypyridin, dadurch gekennzeichnet, dass man       4-Pyridyl-pyridiniumdichlorid    mit Wasser be  handelt. Das so erhaltene Produkt zeigt die  gleichen Eigenschaften wie das bekannte 4  O$ypyridin. Es soll als Zwischenprodukt zum  Beispiel bei der Herstellung von     Farbstoffen       oder pharmazeutischen Produkten Verwen  dung finden.  



  <I>Beispiel:</I>  200     gr    rohes     4-Pyridyl-pyr-idiniumdichlorid     werden in 300 cm' Wasser gelöst und 1 Stunde  auf dem Wasserbad mit 10     gr    Tierkohle er  wärmt. Die Lösung wird noch heiss abgesaugt  und im     Autoklaven    8 Stunden auf 150   er  hitzt oder 48 Stunden am     Rückfluss    gekocht,  mit überschüssigem     Natriumcarbonat    und     darin     wieder mit etwa 10     gr    Tierkohle versetzt und  bis zur breiigen Konsistenz eingedampft.

   Die  ser Brei wird nach dem Erkalten mehrmals  mit absolutem Alkohol ausgezogen, die ver  einigten alkoholischen Auszüge werden im  Vakuum scharf eingedampft, wiederholt mit  Alkohol aufgenommen, wieder zur Trockne  eingedampft, mit Alkohol ausgezogen, von       Natriumchlorid    und     Natriumcarbonat    filtriert,       eingedampt    und schliesslich etwa 1 Stunde  auf etwa 150 erhitzt. Der Rückstand wird  zur weitern Reinigung zweckmässig einer      Destillation unterworfen. Das     4-Oxypyridin     destilliert unter 1 mm Druck bei<B>175-1800</B>  als farbloses 01, das alsbald zu     Kristallen     vom F. 148   erstarrt.

   Man kann auch das     4-          Oxypyridin    in Form seines     schwerlöslichen     Nitrats aus der Reaktionslösung mittelst  Salpetersäure isolieren.



  Process for the preparation of 4-ogypyridine. Through Switzerland. Main patent no.150299, a process for the preparation of 4-aminopyridine is protected, which is characterized in that pyridine is converted into 4-pyridyl-pyridinium dichloride by the action of thioyl chloride and this is converted into 4-aminopyridine by treatment with alkaline agents converts.



  After further processing, it has now been found that 4-pyridyl-pyridinium dichloride is not only a suitable starting material for the preparation of 4-aminopyridine, but can also be converted into other pyridines substituted in the 4-position by the action of hydrogyl-containing substances.



  The present invention now relates to a process for the preparation of -4-ogypyridine, characterized in that 4-pyridyl-pyridinium dichloride is treated with water. The product thus obtained shows the same properties as the known 4 O $ ypyridine. It should be used as an intermediate product, for example in the manufacture of dyes or pharmaceutical products.



  <I> Example: </I> 200 grams of raw 4-pyridyl-pyr-idinium dichloride are dissolved in 300 cm 'of water and heated for 1 hour on a water bath with 10 grams of animal charcoal. The solution is sucked off while still hot and heated in the autoclave to 150 for 8 hours or refluxed for 48 hours, mixed with excess sodium carbonate and then again with about 10 grams of animal charcoal and evaporated to a pulpy consistency.

   After cooling, this paste is extracted several times with absolute alcohol, the combined alcoholic extracts are evaporated sharply in vacuo, repeatedly taken up with alcohol, evaporated to dryness again, extracted with alcohol, filtered from sodium chloride and sodium carbonate, evaporated and finally for about 1 hour heated to about 150. For further purification, the residue is expediently subjected to a distillation. The 4-oxypyridine distills under 1 mm pressure at <B> 175-1800 </B> as a colorless oil, which soon solidifies to crystals of F. 148.

   It is also possible to isolate 4-oxypyridine in the form of its sparingly soluble nitrate from the reaction solution by means of nitric acid.

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Darstellung von 4-Oxypyri- din, dadurch gekennzeichnet, dass man 4-Pyri- dyl-pyridiniumdichlorid der Einwirkung von Wasser unterwirft. Claim: Method for the preparation of 4-oxypyridine, characterized in that 4-pyridyl-pyridinium dichloride is subjected to the action of water.
CH155447D 1931-04-25 1931-04-25 Process for the preparation of 4-oxypyridine. CH155447A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH155447T 1931-04-25

Publications (1)

Publication Number Publication Date
CH155447A true CH155447A (en) 1932-06-30

Family

ID=4409959

Family Applications (1)

Application Number Title Priority Date Filing Date
CH155447D CH155447A (en) 1931-04-25 1931-04-25 Process for the preparation of 4-oxypyridine.

Country Status (1)

Country Link
CH (1) CH155447A (en)

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