Ammonia → HCID 21827056, compound

Participants

Reaction Steps

A suspension of acetamide 232 (2.49 g, 10.5 mmol) and cHCl (10 mL) in EtOH (50 mL) was heated at reflux temperature for 16 h. The solution was cooled, carefully neutralized with aqueous NH3 solution, extracted with EtOAc (2×50 mL), the combined organic fraction dried and the solvent evaporated to give nitroaniline 238 (2.05 g, 100%) as an orange solid: mp (EtOAc) 145-148° C. [lit. (Brancaccio, G.; Lotteiri, G.; Viterbo, R. J. Het. Chem. 1973, 10, 623-629) mp (H2O) 139-140° C.]; 1H NMR δ 7.54 (s, 1H, H-8), 6.50 (s, 1H, H-5), 5.62 (br s, 2H, NH2), 4.14 (br t, J=5.2 Hz, 2H, H-2), 2.77 (br t, J=6.5 Hz, 2H, H-4), 1.95-2.02 (m, 2H, H-3).

Provenance & Evidence