4-Pyridinylacetone → 4-Acetyl-3-methyl-4-(4-pyridinyl)butanenitrile

Temperature

100 °C

To a stirred mixture mixture containing 59.6 g of 1-(4-pyridinyl)propanone and 100 ml of crotononitrile was added a solution of sodium methoxide in methanol obtained by adding 1 pellet of sodium shot to 20 ml of methanol. The reaction mixture was heated on a steam bath with stirring. After about 5 minutes, there was an exothermic reaction which raised the reaction temperature to 100° C. The resulting mixture was allowed to cool to room temperature and stand overnight (about 16 hours). To the reaction was added 100 ml of 10% acetic acid and 300 ml of methylene dichloride; and, the mixture was shaken well. The layers were separated and the methylene dichloride layer was dried over anhydrous magnesium sulfate and filtered. The methylene dichloride was distilled off in vacuo and the residual oil was distilled under vacuum using a small column to produce 85.0 g of 4-acetyl-3-methyl-4-(4-pyridinyl)butanenitrile, b.p. 130°-135° C. at 0.05 mm.

1. customobtained
2. temperatureThe reaction mixture was heated on a steam bath
3. customan exothermic reaction which
4. temperatureto cool to room temperature
5. waitstand overnight
6. custom(about 16 hours)
7. stirringand, the mixture was shaken well
8. customThe layers were separated
9. dry with materialthe methylene dichloride layer was dried over anhydrous magnesium sulfate
10. filtrationfiltered
11. distillationThe methylene dichloride was distilled off in vacuo
12. distillationthe residual oil was distilled under vacuum

ORD record

ord-880e9e8a9a434b4982de76ed6df54d82

Source dataset

uspto-grants-1984_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04431651