Nitric Acid → 6-Bromo-5-nitroquinoline

Participants

Reaction Conditions

Reaction Steps

A solution of 6-bromoquinoline (2.0 g, 9.61 mmol) in concentrated sulfuric acid (10 mL) was cooled to 0° C. Sodium nitrite (27 mg, 0.384 mmol) was added, followed by dropwise addition of concentrated nitric acid (0.8 mL). The reaction mixture was stirred at 0° C. for 45 min. then at room temperature for 1 h, before pouring onto ice, resulting into a yellow precipitate. The mixture was neutralized to pH 7 with ammonium hydroxide. The precipitate was filtered, washed with water and dried in vacuo to yield 2.26 g of 6-bromo-5-nitro-quinoline as a light green solid (93% yield):): 1H NMR (CDCl3) δ 7.62 (dd, 1H), 7.94 (d, 1H), 8.07 (d, 1H), 8.17 (d, 1H), 9.06 (dd, 1H); MS (m/z) 253, 255 [M+H+]+.

Provenance & Evidence