ammonia in methanol T=60°C; 20 h;

1: Et3N / butan-1-ol / 48 h / Heating 2: 1.) 3 N HCl, sodium nitrite, 2.) sodium acetate trihydrate / 1.) water, 2.) acetic acid, water, RT, overnight 3: 66 percent / Zn, acetic acid / H2O; ethanol / 3 h / Heating 4: 81 percent / sodium nitrite, acetic acid / H2O / 1 h / 0 °C 5: 83 percent / liquid ammonia / methanol / 20 h / 60 °C View Scheme

1: 0.5 N aq. barium hydroxide / Heating; overnight 2: Et3N / butan-1-ol / 48 h / Heating 3: 1.) 3 N HCl, sodium nitrite, 2.) sodium acetate trihydrate / 1.) water, 2.) acetic acid, water, RT, overnight 4: 66 percent / Zn, acetic acid / H2O; ethanol / 3 h / Heating 5: 81 percent / sodium nitrite, acetic acid / H2O / 1 h / 0 °C 6: 83 percent / liquid ammonia / methanol / 20 h / 60 °C View Scheme

1: 1.) 3 N HCl, sodium nitrite, 2.) sodium acetate trihydrate / 1.) water, 2.) acetic acid, water, RT, overnight 2: 66 percent / Zn, acetic acid / H2O; ethanol / 3 h / Heating 3: 81 percent / sodium nitrite, acetic acid / H2O / 1 h / 0 °C 4: 83 percent / liquid ammonia / methanol / 20 h / 60 °C View Scheme

1: 81 percent / sodium nitrite, acetic acid / H2O / 1 h / 0 °C 2: 83 percent / liquid ammonia / methanol / 20 h / 60 °C View Scheme

1: 66 percent / Zn, acetic acid / H2O; ethanol / 3 h / Heating 2: 81 percent / sodium nitrite, acetic acid / H2O / 1 h / 0 °C 3: 83 percent / liquid ammonia / methanol / 20 h / 60 °C View Scheme