Hydrochloric Acid → 3-Methanesulfonyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Participants

Reaction Conditions

Reaction Steps

7-Nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine nitrate salt (515 mg/2 mmol) was suspended in methylene chloride (5 mL) and cooled to 0° C. Triethylamine (620 μL/4.4 mmol) was added followed by methanesulfonyl chloride (dropwise, 160 μL/2.1 mmol). After fifteen minutes the reaction was poured into 25 mL of 1 N hydrochloric acid and extracted with methylene chloride (20 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated to give 3-Methanesulfonyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a light brown solid (520 mg/quantitative). 1H NMR (400 MHz, CDCl3) δ 8.05 (m, 2H), 7.3 (d, J=9.1 Hz, 1H), 3.45 (m, 4H), 3.15 (m, 4H), 2.8 (s, 3H).

Provenance & Evidence