hydrogen; palladium on activated charcoal in methanol T=20°C; 1.5 h;

1: 73 percent / hydrazine monohydrate / ethanol / Heating 2: 82 percent / NaNO2; acetic acid / H2O / 0.5 h / 0 °C 3: 71 percent / xylene / Heating 4: H2 / Pd/C / methanol / 1.5 h / 20 °C View Scheme

1: 71 percent / xylene / Heating 2: H2 / Pd/C / methanol / 1.5 h / 20 °C View Scheme

1: 82 percent / NaNO2; acetic acid / H2O / 0.5 h / 0 °C 2: 71 percent / xylene / Heating 3: H2 / Pd/C / methanol / 1.5 h / 20 °C View Scheme