Water → HCID 25139342, compound

Participants

Reaction Conditions

Reaction Steps

Acetamide 155 (24.0 g, 78 mmol) was suspended in MeOH (350 mL), H2O (180 mL) and cHCl (150 mL), and stirred at reflux temperature for 1 h. The resulting orange solution was cooled to 20° C. and the solvent evaporated to give nitroaniline 156 (17.4 g, 100%) as an orange solid: mp 89-91° C.; 1H NMR δ 7.90 (s, 1H, H-4), 6.62 (s, 1H, H-7), 6.02 (br s, 2H, NH2), 3.74 (t, J=6.6 Hz, 2H, CH2O), 2.96-3.04 (m, 2H, H-1, H-3), 2.49-2.60 (m, 3H, H-1, H-2, H-3), 1.77 (q, J=6.6 Hz, 2H, CH2), 1.40 (br s, 1H, OH); 13C NMR δ 153.4, 144.3, 133.0, 131.2, 120.9, 113.5, 61.7, 39.3, 38.2, 37.7, 37.2. Anal. calcd for C11H14N2O3: C, 59.5; H, 6.4; N, 12.6. Found: C, 59.7; H, 6.3; N, 12.2%.

Provenance & Evidence