Acetic Anhydride → 3-Methylpyridine-2-carbonitrile

Participants

Reaction Steps

A 11.53 g (120 mmol) of 2-pyrimidone and 12.14 g (120 mmol) of triethylamine were dissolved in 50 ml of ethanol, and 11.23 g (110 mmol) of acetic anhydride was added dropwise thereto at 70° C. spending 1 hour. The reaction solution was cooled to room temperature and mixed with 8.31 g (100 mmol) of 2-oxobutyronitrile and 30.43 g (400 mmol) of ammonium acetate, and the resulting reaction solution was allowed to undergo the reaction at 80° C. for 4 hours. After completion of the reaction, this was cooled to room temperature, neutralized with 100 g (600 mmol) of 25% sodium hydroxide aqueous solution and then extracted twice with 40 ml of toluene. By concentrating the organic layer, 7.92 g (yield 67.1%) of the title compound was obtained (purity 99.1%, melting point 85-86° C.).

Provenance & Evidence