hydrogenchloride in 1,4-dioxane; dichloromethane T=20°C; 2 h;

hydrogen; nickel in methanol T=21.5 - 25°C; P=2585.7 Torr; 21.5 h;

1: 95 percent / 10percent aq. NaOH / 2 h / 5 °C 2: 91 percent / pyridine / 2 h / 5 °C 3: 98 percent / sodium azide / dimethylformamide / 2 h / 100 °C 4: 95 percent / H2 / Raney nickel / methanol / 21.5 h / 21.5 - 25 °C / 2585.7 Torr View Scheme

1: 91 percent / pyridine / 2 h / 5 °C 2: 98 percent / sodium azide / dimethylformamide / 2 h / 100 °C 3: 95 percent / H2 / Raney nickel / methanol / 21.5 h / 21.5 - 25 °C / 2585.7 Torr View Scheme

1: 98 percent / sodium azide / dimethylformamide / 2 h / 100 °C 2: 95 percent / H2 / Raney nickel / methanol / 21.5 h / 21.5 - 25 °C / 2585.7 Torr View Scheme

sodium hydroxide in tert-butyl alcohol Ambient temperature;