反应详情

8-Chloro-2,5-dihydro-2,5-dioxo-3-methoxy-1H-benz[b]azepine [Formula II: RI=R2 =R4 =H; R3Cl; R5 =CH3 ](0.0789 g, 0.332 mM) was added to a solution of 1.01 mL (1.OM, CH2Cl2) boron tribromide in 1.8 mL dry methylene chloride under nitrogen. The suspension was stirred at room temperature for 0.42 hours. The reaction mixture was poured into 7 mL of saturated aqueous sodium bicarbonate and stirred for 0.25 hours. The homogeneous solution was then adjusted to pH=5 by slow addition of concentrated hydrochloric acid. The precipitate was vacuum filtered and washed with water to give 0.0683 g (92%) of white solid which was recrystallized from 5 mL DMF and 1 mL of water. After cooling in an ice bath, solid was collected by vacuum filtration, washed with water and vacuum dried at 100° C. and 15 Pato give 0.056 g (75%) of product; mp 308.5-310.5 (dec); NMR (DMSO-d6, 300 MHz): 11.57 (s,1H, N--H), 10.86 (brs,1H, O--H), 8.04 (d,1H, Jortho =8.7 Hz), 7.54 (d,1H, Jmeta =2.0 Hz), 7.31 (dd,1H, Jortho =8.7, Jmeta =2.0 Hz), 6.41 (s,1H);

1. stirringstirred for 0.25 hours
2. filtrationfiltered
3. washwashed with water