Nitric Acid → 6-Acetamido-5-nitro-1-tetralone

Participants

Reaction Conditions

Reaction Steps

6-Acetamido-tetralone (15 g) was added in small portions to a cold solution of nitric acid (46 ml) at -30° C. After the addition was complete (2-3 hours), the reaction mixture was stirred at the same temperature for 1 hour, warmed to 0° C. and stirred for 4 hours. The reaction was poured on ice, basified with aqueous sodium hydroxide and extracted with ethyl acetate several times. The organic layer was separated, dried and evaporated. The desired 5-nitro-isomer was separated using flash chromatography (ethyl acetate-methylene chloride) to afford 8.73 g (48%).

Provenance & Evidence