Hydrochloric Acid → Phenol, 3-(methylamino)-4-nitro-

Participants

Reaction Conditions

Reaction Steps

To a pressure vessel was added 3-fluoro-4-nitro-phenol (5.0 g, 31.82 mmol) and a 40% aqueous solution of methylamine (10 mL). The reaction mixture was stirred at 85° C. for 5 h, then it was cooled to room temperature, poured on water, and acidified to pH 1 with 1 N aqueous HCl. The resulting precipitate was filtered, washed with water, and dried in vacuo to give 5.23 g of 3-methylamino-4-nitro-phenol as an orange solid (98% yield): 1H NMR (DMSO-d6) δ 2.88 (d, 3H), 6.14 (dd, 1H), 6.17 (d, 1H), 7.96 (d, 1H), 8.25 (q, 1H), 10.8 (broad s, 1H); MS (m/z) 167 [M−H]−.

Provenance & Evidence