Iodoethane → HCID 67264711, compound

Participants

Reaction Steps

To a solution of 6-methoxy-7-nitro-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (4.5 g, 19.0 mmol) in dimethylformamide (30 mL) at 0° C. was added sodium hydride (60% on mineral oil, 1.15 g, 28.5 mmol) in small portions within 30 minutes. The mixture was stirred for 30 minutes at this temperature followed by adding ethyl iodide (1.84 mL, 22.9 mmol) dropwise. The mixture was warmed to room temperature and stirred for another 2 hours. Upon completion, the mixture was poured into ice-water and filtered to afford the product 1-ethyl-6-methoxy-7-nitro-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one as a off-white solid (3.77 g, yield 78.5%). 1H NMR (400 MHz, CDCl3) δ ppm 7.81-7.84 (dd, 1H, J=1.6 Hz, 8.8 Hz), 7.08-7.10 (dd, 1H, J=1.2 Hz, 8.8 Hz), 3.76-3.94 (s+m, 5H), 2.89-2.96 (m, 2H), 2.22-2.32 (m, 4H), 1.16-1.26 (m, 3H).

Provenance & Evidence