Hydrochloric Acid → 4-Ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of potassium 2-methylpropan-2-olate (4.92 g, 43.81 mmol) and 2-cyanoacetamide (4.05 g, 48.19 mmol) in (methylsulfinyl)methane (60 mL) was added hex-3-en-2-one (4.30 g, 43.81 mmol) under nitrogen atmosphere at 25° C. The reaction mixture was then stirred at 25° C. for 30 min, and then additional potassium 2-methylpropan-2-olate (14.75 g, 131.44 mmol) was added. Nitrogen gas was displaced by oxygen gas and the mixture was stirred at 25° C. for 48 hr. The mixture was diluted with 4 volumes water (240 mL), and then 5 volumes of 4 N HCl (300 mL), which were added slowly. The reaction mixture was filtered, washed with water, and dried to give 4-ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (1.30 g, 18.3%) as a gray solid.

Provenance & Evidence