Hydrochloric Acid → 2-Iodo-3-nitrobenzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2-(acetylamino)-3-nitrobenzoate (4.19 g, 17.6 mmol) and potassium hydroxide (4.93 g, 88.0 mmol) in water (20 mL) was stirred at 60° C. overnight. The resulting solid was collected by filtration, washed with methanol, and is suspended in water (14 mL). Concentrated hydrochloric acid (7.3 mL, 88 mmol) was added to the suspension, and a solution of sodium nitrite (1.88 g, 27.3 mmol) in water (10 mL) was added at 0° C. over 1.5 hr. The reaction mixture was added to a solution of potassium iodide (4.53 g, 27.3 mmol) and iodine (3.73 g, 14.7 mmol) in dimethyl sulfoxide (130 mL) at 5° C. over 20 min. The resulting reaction mixture was stirred at 50° C. for 20 min, and extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with hexane to give the title compound (3.71 g, yield 72%).

Provenance & Evidence