Reaction Steps
To a hot solution of 14l (110 mg, 0.26 mmol) in THF (10 mL) was added in sequential fashion MeOH (5 mL), H2O (2 mL), AcOH (0.2 mL) and Fe powder (0.5 mL). The mixture was heated at reflux for 1 h, then basified with CaO (1 g), filtered, concentrated to a small volume under reduced pressure below 30° C. and diluted with water. The resulting precipitate was chromatographed on silica gel, eluting with CH2Cl2 /EtOAc (9:1), to give a solid which was recrystallised from CH2Cl2 /petroleum ether to give 15l (55 mg, 54%) mp >200° C. 1H NMR [(CD3)2SO] δ 8.06 (d, J=8.5 Hz, 1 H, H-6), 7.83 (bs, 1 H, H-4), 7.72 (d, J=8.3 Hz, 1 H, H-9), 7.63 (d, J=15.4 Hz, 1 H, PhC=CH), 7.44 (t, J=7.4 Hz, 1 H, H-8), 7.40-7.34 (m, 3 H, PhH), 7.26 (t, partially obscured, J=7.9 Hz, 1 , H-7), 7.22 (d, J=15.4 Hz, 1 h, PhCH=CH), 7.04-6.97 (m, 1 H, PhH), 5.95 (br s, 2 H, NH2), 4.53-4.38 (m, 2 H, H-2), 4.19-4.08 (m, 1 H, H-1), 3.95 (dd, J=11.0, 2.9 Hz, 1 H, CHHCl), 3.83 (s, 3 H, OCH3), 3.76 (dd, J=10.9, 8.1 Hz, 1 H, CHHCl). Anal. Calculated for C23H21ClN2O2 : C, 70.3; H, 5.4; N, 7.1; Cl, 9.0. Found: C, 70.4; H, 5.6; N, 6.9; Cl, 9.1%.
