Ammonia → 6-Nitro-2,3-dihydrobenzofuran-5-amine

Participants

Reaction Steps

A suspension of acetamide 193 (8.98 g, 40.4 mmol) and cHCl (50 mL) in EtOH (100 mL) was heated at reflux temperature for 2 h. The solution was cooled, carefully neutralized with aqueous NH3 solution, and the resulting precipitate filtered and dried to give nitroaniline 194 (7.27 g, 100%) as an orange solid: mp (H2O) 148-149° C.; 1H NMR δ 7.44 (s, 1H, H-7), 6.68 (t, J=1.2 Hz, 1H, H-4), 5.92 (br s, 2H, NH2), 4.54 (t, J=8.4 Hz, 2H, H-2), 3.18 (dt, J=8.4, 1.2 Hz, 2H, H-3); 13C NMR δ 151.8, 140.8, 139.0, 131.2, 114.4, 103.4, 71.2, 30.0. Anal. calcd for C8H8N2O3: C, 53.3; H, 4.5; N, 15.6. Found: C, 53.2; H, 4.5; N, 15.6%.

Provenance & Evidence