Sodium Hydroxide → HCID 21827055, compound

Participants

Reaction Steps

A solution of acetamide 231 (1.24 g, 5.25 mmol) in 95% EtOH (50 mL) and NaOH (0.63 g, 15.7 mmol) was stirred at reflux temperature for 16 h. The mixture was cooled and the solvent evaporated. The residue was partitioned between Et2O and water, the organic fraction dried and the solvent evaporated. The residue was purified by chromatography, eluting with 20% EtOAc/pet. ether, to give nitroaniline 233 (1.54 g, 85%) as red oil: 1H NMR δ 6.85 (d, J=9.0 Hz, 1H, H-8), 6.60 (d, J=9.0 Hz, 1H, H-7), 4.90 (br s, 2H, NH2), 4.13 (dd, J=5.3, 5.1 Hz, 2H, H-2), 2.90 (br t, J=6.5 Hz, 2H, H-4), 1.91-1.96 (m, 2H, H-3).

Provenance & Evidence