ammonia in ethanol T=140°C; 60 h;

sodium nitrite in acetic acid 15 h;

sodium hydroxide T=95 - 100°C;

1: 86 percent / 2 h / 80 °C 2: 41 percent / triethylamine / dimethylformamide / 15 h / Ambient temperature 3: 32 percent / Zn powder / acetic acid / 1.5 h / Heating 4: 84 percent / 40percent aq. methylamine / 1 h / 100 °C 5: 48 percent / NaNO2 / acetic acid / 15 h View Scheme

1: 41 percent / triethylamine / dimethylformamide / 15 h / Ambient temperature 2: 32 percent / Zn powder / acetic acid / 1.5 h / Heating 3: 84 percent / 40percent aq. methylamine / 1 h / 100 °C 4: 48 percent / NaNO2 / acetic acid / 15 h View Scheme

1: 84 percent / 40percent aq. methylamine / 1 h / 100 °C 2: 48 percent / NaNO2 / acetic acid / 15 h View Scheme

1: 32 percent / Zn powder / acetic acid / 1.5 h / Heating 2: 84 percent / 40percent aq. methylamine / 1 h / 100 °C 3: 48 percent / NaNO2 / acetic acid / 15 h View Scheme

1: 82 percent / 1N NaOH / methanol / 2.5 h / ice-bath 2: 5 percent / 6N NaOH / 95 - 100 °C View Scheme