Water → 8-amino-4-(3-bromophenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of compound 3 (0.1 g, 0.27 mmol) in EtOH:H2O (10 mL, 6:3) was added Fe-powder (0.076 g, 1.39 mmol) followed by NH4Cl (0.037 g, 0.70 mmol) at RT. The resulting reaction mixture was heated to 90° C. and stirred for 1 h; progress of the reaction was monitored by TLC. The reaction mixture was then cooled to RT; the reaction mixture was filtered and the obtained filtrate was concentrated under reduced pressure. The residue was diluted with water (10 mL) and then extracted with EtOAc (2×10 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 4 (35 mg, 38%) as yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.32 (bs, 1H), 8.15-8.13 (m, 1H), 7.97 (d, J=7.6 Hz, 1H), 7.69 (d, J=7.2 Hz, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.12 (d, J=8.8 Hz, 1H), 6.52 (d, J=8.4 Hz, 1H), 6.32 (s, 1H), 5.48 (bs, 2H), 3.42 (s, 2H). Mass: m/z 331 [M+1]+

Provenance & Evidence