hydrazine hydrate; palladium on activated charcoal in ethanol 0.5 h; Heating;

1: 44 percent / bromine, aq. NaOH / 1.) 0 deg C, 0.5 h, 2.) RT, 2 h 2: 79 percent / potassium carbonate / dimethylsulfoxide / 1 h / Heating 3: 45 percent / nitric acid, conc. sulfuric acid / 2 h / 60 - 65 °C 4: 95 percent / sodium methoxide / methanol / 20 h 5: hydrazine hydrate / Pd/C / ethanol / 0.5 h / Heating View Scheme

1: 79 percent / potassium carbonate / dimethylsulfoxide / 1 h / Heating 2: 45 percent / nitric acid, conc. sulfuric acid / 2 h / 60 - 65 °C 3: 95 percent / sodium methoxide / methanol / 20 h 4: hydrazine hydrate / Pd/C / ethanol / 0.5 h / Heating View Scheme

1: 95 percent / sodium methoxide / methanol / 20 h 2: hydrazine hydrate / Pd/C / ethanol / 0.5 h / Heating View Scheme

1: 45 percent / nitric acid, conc. sulfuric acid / 2 h / 60 - 65 °C 2: 95 percent / sodium methoxide / methanol / 20 h 3: hydrazine hydrate / Pd/C / ethanol / 0.5 h / Heating View Scheme