hydrogen; palladium on activated charcoal in ethyl acetate P=2700.2 Torr; 7.5 h; Ambient temperature;

1: 49 percent / dimethylformamide / 6 h / Heating 2: 96 percent / H2 / 10percent Pd/C / ethyl acetate / 7.5 h / 2700.2 Torr / Ambient temperature View Scheme

1: HCl, NaNO2 / Ambient temperature 2: 49 percent / dimethylformamide / 6 h / Heating 3: 96 percent / H2 / 10percent Pd/C / ethyl acetate / 7.5 h / 2700.2 Torr / Ambient temperature View Scheme

1: 31 percent / aq. HCl, NaNO2 / 3 h / Ambient temperature 2: 52 percent / dimethylformamide / 8 h / Heating 3: 68 percent / aq. NaOH / methanol / 1 h / Ambient temperature 4: diphenylphosphoric azide, Et3N / 2-methyl-propan-2-ol / 3 h / Heating 5: H2O / 1 h / Heating View Scheme

1: 52 percent / dimethylformamide / 8 h / Heating 2: 68 percent / aq. NaOH / methanol / 1 h / Ambient temperature 3: diphenylphosphoric azide, Et3N / 2-methyl-propan-2-ol / 3 h / Heating 4: H2O / 1 h / Heating View Scheme

1: diphenylphosphoric azide, Et3N / 2-methyl-propan-2-ol / 3 h / Heating 2: H2O / 1 h / Heating View Scheme