Ammonium Hydroxide → 5-Bromo-8-nitroisoquinoline

Participants

Reaction Steps

A solution of potassium nitrate (1.78 g, 8.56 mmol) in 2 ml concentrated H2SO4 was added slowly to a solution of 5-bromoisoquinoline in 12 mL concentrated H2SO4. After stirring for 3 hours the reaction mixture was poured onto ice and neutralized with conc. ammonium hydroxide. The yellow precipitate was extracted with ethyl acetate (3×), and the combined organic layers were washed with saturated NaCl, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel (40% ethyl acetate in hexane as eluent) to give 5-bromo-8-nitroisoquinoline.

Provenance & Evidence