1: 69 percent / POCl3 / 2 h / 80 °C 2: 69 percent / KOH / 2-ethoxy-ethanol / 8 h / Heating 3: 75 percent / H2 / Raney Ni / ethanol; dioxane / 1.25 h / 2327.2 Torr 4: 57 percent / Et3N / 2-ethoxy-ethanol / 6.5 h / 105 °C 5: hydrazine hydrate / ethanol / 6 h / Heating View Scheme

1: 57 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C 2: 67 percent / Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C 3: 90 percent / Et3N / 4.5 h / 140 - 150 °C 4: 95percent aq. H2NNH2 / ethanol / 4.5 h / Heating View Scheme

1: 69 percent / POCl3 / 2 h / 80 °C 2: 69 percent / KOH / 2-ethoxy-ethanol / 8 h / Heating View Scheme

1: 69 percent / POCl3 / 2 h / 80 °C 2: 64 percent / KOH / 2-ethoxy-ethanol / 8 h / Heating View Scheme