1-Chloro-2-nitrobenzene → 2-Chlorophenylhydroxylamine

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-chloronitrobenzene (50 g, 0.318 mol) and ammonium chloride (16.9 g, 0.318 mmol) in 636 mL of water was warmed to 65° C. To the mixture was added in portions zinc (60 g, 0.955 mol) over 20 min, and the temperature was kept at 70° C.˜75° C. After stirring for 10 min, TLC showed the reaction was completed. The mixture was filtered and washed with water (˜70° C.). To the filtrate was added NaCl, then cooled to −10° C. After 1 h, the mixture was filtered and washed with pertrolume, and then dried to afford the desired hydroxylamine as a white solid (35 g, 76.9%), which was used to next step without purification. 1HNMR (400 MHz, DMSO): δ 8.36 (s, 2H), 7.16 (m, 2H), 6.79 (m, 2H).

Provenance & Evidence