Nitric Acid → 4-(4-Nitrophenyl)pyridine

Participants

Reaction Steps

In a 300-ml four-necked flask were placed 206.2 g (2.10 moles) of concentrated sulfuric acid and 19.6 g (0.19 mole) of 60% nitric acid. The mixture was stirred on an ice bath and 25.7 g (0.17 mole) of 4-phenylpyridine was added at 0° C. After the addition, the stirring was continued at 0° C. for three hours. The reaction mixture thus prepared was added in drops to 1250.0 g of ice placed in a 2000-ml four-necked flask. The mixture was stirred on an ice bath and 600.6 g (4.43 moles) of a 29.5% aqueous solution of sodium hydroxide was added in drops. Thereafter, a solid was recovered by filtration at 0° C. The solid was washed with water and recrystallized twice from 200 ml of 5M hydrochloric acid. To the solid thus obtained was added 200 ml of 5M hydrochloric acid in drops. The solid was dissolved by heating and 201.4 g (1.49 moles) of a 29.5% aqueous solution of sodium hydroxide was added in drops. The mixture was cooled to room temperature and a separated solid was recovered by filtration. The solid was washed with water and dried under reduced pressure to give 12.9 g of 4-(4-nitrophenyl)pyridine.

Provenance & Evidence