Acetic Anhydride → HCID 118307491, compound

Participants

Reaction Steps

To a solution of compound 13 (2.5 g, 10.82 mmol) in pyridine (20 mL) was added acetic anhydride (2 mL, 21.60 mmol) and the mixture was stirred at room temperature for 12 h. The reaction was added ethyl acetate (30 mL) and the organic layer was washed sequentially with H2O (20 mL), 1N HCl (15 mL×3), brine (15 mL) and dried over Na2SO4 and evaporated to get the title compound as an off-white solid (2.89 g, 98%). IR (KBr) νmax. cm−1: 3419 (NH), 3062 (Ar—H), 2925 (Alph-H), 1695 (C═O), 1604, 1564 (C═C), 1520, 1435 (NO2), 1232 (C—N), 1168 (C—O). 1H NMR (500 MHz, CDCl3) δ=2.19 (s, 3H, CH3); 5.50 (s, 2H, CH2); 7.63 (dd, 1H, J=2.3, 8.6 Hz, H-4); 7.75 (d, 1H, J=2.3, H-6), 8.00 (d, 1H, J=8.6 Hz, H-3). 13C NMR (125.7 MHz, CDCl3) δ=20.78 (CH3), 62.27 (CH2), 126.58 (C-3), 129.03 (C-1), 131.73 (C-6), 131.82 (C-4), 134.34 (C-5), 145.33 (C-2), 170.10 (CO). Calculated (%) for C9H9BrN2O3 (271.98); C, 39.58; H, 3.32; N, 10.26. found (%); C, 39.52; H, 3.36; N, 10.20.

Provenance & Evidence