hydrogen; nickel in methanol T=20°C; P=760 Torr;

1: hydrazine hydrate / ethanol / 4 h / Heating 2: 1.) Br2, 2.) NaOAc / 1.) AcOH, 80 deg C, 2 h, 2.) AcOH, reflux, 1 h 3: phosphorus oxychloride / 4 h / 85 - 95 °C 4: hydrazine hydrate / butan-1-ol / 6 h / 100 °C 5: H2 / Raney Ni / methanol / 20 °C / 760 Torr View Scheme

1: phosphorus oxychloride / 4 h / 85 - 95 °C 2: hydrazine hydrate / butan-1-ol / 6 h / 100 °C 3: H2 / Raney Ni / methanol / 20 °C / 760 Torr View Scheme

1: hydrazine hydrate / butan-1-ol / 6 h / 100 °C 2: H2 / Raney Ni / methanol / 20 °C / 760 Torr View Scheme

1: 1.) Br2, 2.) NaOAc / 1.) AcOH, 80 deg C, 2 h, 2.) AcOH, reflux, 1 h 2: phosphorus oxychloride / 4 h / 85 - 95 °C 3: hydrazine hydrate / butan-1-ol / 6 h / 100 °C 4: H2 / Raney Ni / methanol / 20 °C / 760 Torr View Scheme

1: NaOH, H2O / ethanol / 50 °C 2: hydrazine hydrate / ethanol / 4 h / Heating 3: 1.) Br2, 2.) NaOAc / 1.) AcOH, 80 deg C, 2 h, 2.) AcOH, reflux, 1 h 4: phosphorus oxychloride / 4 h / 85 - 95 °C 5: hydrazine hydrate / butan-1-ol / 6 h / 100 °C 6: H2 / Raney Ni / methanol / 20 °C / 760 Torr View Scheme