in water T=80°C; 1 h;

1: 1. Br2 / Ambient temperature; 1. CCl4, irradiation, reflux, 4h; 2. r.t., overnight 2: 12N hydrochloric acid / ethanol / Ambient temperature; overnight 3: 86 percent / acetic acid / 0.08 h / Heating 4: 64 percent / HCl (g) / diethyl ether / 10 degC, 3h, then r.t., overnight 5: 83 percent / H2O / 1 h / 80 °C View Scheme

1: 86 percent / acetic acid / 0.08 h / Heating 2: 64 percent / HCl (g) / diethyl ether / 10 degC, 3h, then r.t., overnight 3: 83 percent / H2O / 1 h / 80 °C View Scheme

1: hydrazine hydrate / ethanol / 4 h / Heating 2: 86 percent / acetic acid / 0.08 h / Heating 3: 64 percent / HCl (g) / diethyl ether / 10 degC, 3h, then r.t., overnight 4: 83 percent / H2O / 1 h / 80 °C View Scheme

1: 85 percent / dimethylformamide / 3 h / Heating 2: hydrazine hydrate / ethanol / 4 h / Heating 3: 86 percent / acetic acid / 0.08 h / Heating 4: 64 percent / HCl (g) / diethyl ether / 10 degC, 3h, then r.t., overnight 5: 83 percent / H2O / 1 h / 80 °C View Scheme

1: 64 percent / HCl (g) / diethyl ether / 10 degC, 3h, then r.t., overnight 2: 83 percent / H2O / 1 h / 80 °C View Scheme

1: 12N hydrochloric acid / ethanol / Ambient temperature; overnight 2: 86 percent / acetic acid / 0.08 h / Heating 3: 64 percent / HCl (g) / diethyl ether / 10 degC, 3h, then r.t., overnight 4: 83 percent / H2O / 1 h / 80 °C View Scheme

1: 87 percent / triethylamine / toluene / 6 h / 95 °C / r.t., overnight 2: H2 / PtO2 / ethyl acetate / 3.5 h / Ambient temperature 3: H2 / PtO2 / acetic acid; ethyl acetate / 1.5 h / Ambient temperature 4: 90 percent / triethylamine / tetrahydrofuran / Ambient temperature; overnight 5: 96 percent / H2 / 5percent Pd-on-carbon / acetic acid; ethanol / 1.5 h / 40 °C / 2280 Torr 6: 1M diborane / tetrahydrofuran / 1 h / Heating View Scheme