pyridine; 7,8-methylenedioxy-4,5-dihydro-3H-3-benzazepine in benzene T=20°C; 12 h;

thionyl chloride in benzene 1 h; Heating;

sodium hydroxide; thionyl chloride; 1,3-dibromo-5,5-dimethyl-hydantoin Multistep reaction;

1: 70 percent / KMnO4 / acetone; H2O / 3 h / 50 - 60 °C 2: 90.7 percent / SOCl2 / benzene / 1 h / Heating View Scheme

1: 96 percent / K2CO3 / dimethylformamide / 5 h / 110 - 120 °C 2: 70 percent / KMnO4 / acetone; H2O / 3 h / 50 - 60 °C 3: 90.7 percent / SOCl2 / benzene / 1 h / Heating View Scheme

1: 1.) Br2, KBr, 2.) NaOH / 1.) H2O, 6 h, 2.) H2O, 6 h 2: 96 percent / K2CO3 / dimethylformamide / 5 h / 110 - 120 °C 3: 70 percent / KMnO4 / acetone; H2O / 3 h / 50 - 60 °C 4: 90.7 percent / SOCl2 / benzene / 1 h / Heating View Scheme

1: 1.01 g / Et3N / CH2Cl2 / 1 h / 20 °C 2: 93 percent / NaH / dimethylformamide / 5 h / 20 °C 3: 96 percent / Ag2CO3 / Pd(OAc)2; P(o-Tol)3 / dimethylformamide / 3 h / Heating View Scheme

1.1: Et3N; DMAP / CH2Cl2 / 20 °C 2.1: KHMDS / toluene / 0 - 20 °C 2.2: 47 percent / toluene 3.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C 4.1: 77 percent / PPh3; aq. NaOH / Pd(OAc)2 / tetrahydrofuran / Heating 5.1: H2 / Pd/C / methanol / 20 °C 6.1: 60 percent / H2SO4 / acetic acid / 20 °C 7.1: 65 percent / H2 / Pd/C / acetic acid / 20 °C View Scheme