T=190°C;

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 5: 87 percent / triethylamine / toluene / 6 h / 95 °C / r.t., overnight 6: H2 / PtO2 / ethyl acetate / 3.5 h / Ambient temperature 7: H2 / PtO2 / acetic acid; ethyl acetate / 1.5 h / Ambient temperature 8: 90 percent / triethylamine / tetrahydrofuran / Ambient temperature; overnight 9: 96 percent / H2 / 5percent Pd-on-carbon / acetic acid; ethanol / 1.5 h / 40 °C / 2280 Torr 10: 1M diborane / tetrahydrofuran / 1 h / Heating View Scheme

1: hydrazine hydrate / ethanol / 4 h / Heating 2: 86 percent / acetic acid / 0.08 h / Heating 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

T=190°C;

T=190°C;