Hydrochloric Acid → HCID 85439451, compound

Participants

Reaction Steps

Hydrochloric acid gas was bubbled through a cooled suspension of 1-tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one (30 g, 0.1 mol) in a dry diethyl ether (500 mL) at 0-5° C. Isoamyl nitrite (26.41 mL, 0.24 mol) was added drop wise and hydrochloric acid gas was continuously passed for 6-7 h after the addition. The precipitate that formed was filtered washed with diethyl ether and dried under reduced pressure to afford 4-(hydroxyimino)-1-tosyl-3,4-dihydro-1H-benzo[b]azepin-5 (2H)-one (21.09 g). 1H NMR: 400 MHz, CDCl3) δ: 7.79 (1H, d, J=7.6 Hz), 7.2 (1H, t, J=7.6 Hz), 7.62 (1H, d, J=8.0 Hz), 7.55 (1H, t, J=7.2 Hz), 7.39 (2H, d, J=8.4 Hz), 7.16 (2H, d, J=8.4 Hz), 4.07 (2H, t, J=6.8 Hz), 2.88 (2H, t, J=6.8 Hz), 2.342 (3H, s), 1.98 (2H, m).

Provenance & Evidence