Diethyl Ether → HCID 117759578, compound

Participants

Reaction Steps

To a solution of compound (14) (0.5 g, 2.5 mmol) in pyridine (5 mL) was added acetic anhydride (0.95 mL, 10 mmol), and the reaction was stirred overnight at room temperature. To the mixture was added diethyl ether (20 mL), and the mixture was washed successively with H2O (10 mL), 1M HCl (10 mL), and brine (10 mL). The organic layer was dried over Na2SO4 and evaporated to obtain 0.70 g (99%) of compound 15 as an off-white solid. IR (KBr) νmax. cm−1: 3312 (NH), 3042 (Ar—H), 1690 (C═O), 1522, 1410 (C═C). 1H NMR (500 MHz, CDCl3) δ=2.11 (s, 3H, CH3); 2.23 (s, 3H, CH3); 5.05 (s, 2H, CH2); 7.46 (m, 2H, H-3, H-5); 7.89 (d, 1H, J=8.2 Hz, H-6). Calculated (%) for C11H13BrN2O2 (284.02); C, 46.33; H, 4.60; N, 9.82. found (%); C, 46.28; H, 4.63; N, 9.76.

Provenance & Evidence