hydrogen; Lindlar's catalyst in ethanol T=25°C; P=2585.7 Torr; 23 h;

lithium aluminium tetrahydride in tetrahydrofuran Heating;

1: 88 percent / thionyl chloride / 24 h / Heating 2: 66 percent / NH3 / methanol / 96 h 3: LiAlH4 / tetrahydrofuran / 24 h / Heating View Scheme

1.1: sodium; n-EtOH / ethanol / 24 h / Heating 1.2: aq. HCl / dimethylformamide / 24 h / Heating 2.1: 88 percent / thionyl chloride / 24 h / Heating 3.1: 66 percent / NH3 / methanol / 96 h 4.1: LiAlH4 / tetrahydrofuran / 24 h / Heating View Scheme

1: 68 percent / sodium azide, manganese(III) acetate / acetic acid / 116 °C 2: H2 / Lindlar's catalyst / ethanol / 23 h / 25 °C / 2585.7 Torr View Scheme

1: (i) SOCl2, (ii) aq. NH3 2: liq. NH3 / 60 °C / 18387.7 Torr 3: LiAlH4 / tetrahydrofuran / Heating View Scheme

1: liq. NH3 / 60 °C / 18387.7 Torr 2: LiAlH4 / tetrahydrofuran / Heating View Scheme