N-(5-Ethoxy-2-nitrophenyl)acetamide → 5-ethoxy-2-nitroaniline

Participants

Reaction Steps

A suspension of N-(5-ethoxy-2-nitrophenyl)acetamide (2.3 g, 10.3 mmol) in 5 M HCl (50 mL) was stirred at reflux temperature for 8 h. The resulting solution was cooled, diluted with water (200 mL), the resulting precipitate filtered and washed with water (2×10 mL) and dried to give aniline 15 (1.70 g, 90%) as an orange powder, mp (H2O) 101-102° C.; 1H NMR δ 8.06 (d, J=9.5 Hz, 1 H, H-3), 6.27 (dd, J=9.5, 2.6 Hz, 1 H, H-4), 6.13 (d, J=2.6 Hz, 1 H, H-6), 5.80 (br s, 2 H, NH2), 4.04 (q, J=7.0 Hz, 2 H, CH2O), 1.42 (t, J=7.0 Hz, 3 H, CH3); 13C NMR δ 164.8, 147.1, 128.4, 126.8, 106.9, 99.0, 64.1, 14.5. Anal. Calcd for C8H10N2O3: C, 52.7; H, 5.5; N, 15.4. Found: C, 52.6; H, 5.5; N, 15.4%.

Provenance & Evidence