lithium aluminium tetrahydride in diethyl ether

1.1: 99 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr 2.1: H2SO4 / H2O / 1 h / 20 °C 2.2: NaNO2 / H2O / 1.5 h / 10 °C 2.3: 84 percent / KI; Cu powder / H2O / 30 °C 3.1: 90 percent / SOCl2 / 3 h / Heating 4.1: 93 percent / Cu / dimethylformamide / 5.5 h / Heating 5.1: 100 percent / LiAlH4 / diethyl ether / 5 h / Heating View Scheme

1.1: 46 percent / HNO3 / 1 h / -10 °C 2.1: 99 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr 3.1: H2SO4 / H2O / 1 h / 20 °C 3.2: NaNO2 / H2O / 1.5 h / 10 °C 3.3: 84 percent / KI; Cu powder / H2O / 30 °C 4.1: 90 percent / SOCl2 / 3 h / Heating 5.1: 93 percent / Cu / dimethylformamide / 5.5 h / Heating 6.1: 100 percent / LiAlH4 / diethyl ether / 5 h / Heating View Scheme

1: 1.) NaH, 2.) benzylamine / 1.) THF, room temperature, 30 min, 2.) THF, reflux 2: 63 percent / CuCN, O2 / tetrahydrofuran / 1.) -78 deg C, 2 h, 2.) 0 deg C, 1 h 3: 87 percent / H2 / Pd/C / methanol / 24 h View Scheme

1.1: H2SO4 / H2O / 1 h / 20 °C 1.2: NaNO2 / H2O / 1.5 h / 10 °C 1.3: 84 percent / KI; Cu powder / H2O / 30 °C 2.1: 90 percent / SOCl2 / 3 h / Heating 3.1: 93 percent / Cu / dimethylformamide / 5.5 h / Heating 4.1: 100 percent / LiAlH4 / diethyl ether / 5 h / Heating View Scheme

1: 90 percent / SOCl2 / 3 h / Heating 2: 93 percent / Cu / dimethylformamide / 5.5 h / Heating 3: 100 percent / LiAlH4 / diethyl ether / 5 h / Heating View Scheme

lithium aluminium tetrahydride

1: H2O2 3: H2SO4 4: LiAlH4 View Scheme

phosphorus tribromide in toluene