hydrogen; nickel in ethanol P=2327.2 Torr; 1 h;

1: 92 percent / conc. HCl / ethanol / 21 h / Heating 2: 69 percent / POCl3 / 2 h / 80 °C 3: 69 percent / KOH / 2-ethoxy-ethanol / 8 h / Heating 4: 75 percent / H2 / Raney Ni / ethanol; dioxane / 1.25 h / 2327.2 Torr 5: 57 percent / Et3N / 2-ethoxy-ethanol / 6.5 h / 105 °C 6: hydrazine hydrate / ethanol / 6 h / Heating View Scheme

1: 92 percent / conc. HCl / ethanol / 21 h / Heating 2: 69 percent / POCl3 / 2 h / 80 °C 3: 69 percent / KOH / 2-ethoxy-ethanol / 8 h / Heating View Scheme

1: 92 percent / conc. HCl / ethanol / 21 h / Heating 2: 69 percent / POCl3 / 2 h / 80 °C 3: 64 percent / KOH / 2-ethoxy-ethanol / 8 h / Heating View Scheme