Hydrochloric Acid → 4-Hydrazinobenzonitrile

To a mixture of 100 g of 4-aminobenzonitrile, 500 ml of water and 360 g of concentrated hydrochloric acid, a liquid mixture of 60.2 g of sodium nitrite and 240 ml of water was added at 0° C., and the resulting mixture was stirred for 30 minutes. The mixture was added to a liquid mixture of 382 g of stannous chloride dihydrate and 480 g of concentrated hydrochloric acid at 15° C., and the resulting crystals were collected by filtration, washed with water and then suspended in 1,000 ml of water. 300 ml of 5N aqueous sodium hydroxide was added to the suspension, and the resulting mixture was stirred for 1.5 hours. The resulting crude product was washed with water and recrystallized in benzene to give 70.2 g of the title compound as pale brown crystals.

1. additionwas added at 0° C.
2. filtrationthe resulting crystals were collected by filtration
3. washwashed with water
4. addition300 ml of 5N aqueous sodium hydroxide was added to the suspension
5. stirringthe resulting mixture was stirred for 1.5 hours
6. washThe resulting crude product was washed with water
7. customrecrystallized in benzene

ORD record

ord-83fb61ef7e25403a988f87322302c4ea

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05968967