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
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)
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) |
-
1931
- 1931-04-25 CH CH155447D patent/CH155447A/en unknown
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