Acetic Acid → 2(3h)-Benzoxazolone, 5-chloro-6-nitro-

Participants

Reaction Conditions

Reaction Steps

In a 250-ml flask, place 17.0 g (0.1 m) of chlorzoxazone (1b; X=Cl), 50 ml of acetic acid, and 0.14 g of sodium nitrite. Warm and stir the slurry to 50° C. Add 11.3 g (0.125 m) of concentrated nitric acid (70%) and stir the mixture at 55°-63° C. for 5 hrs. Add 100 ml of hot water, cool to room temperature and let it stand overnight. Collect solid, wash with water, and dry in air to give 18.7 g (87%) of 5-chloro-6-nitro-benzoxazol-2-one (2b; X=Cl) as pale yellow solids.

Provenance & Evidence