water

ammonium hydroxide; hydrogen; palladium on activated charcoal in ethanol; water P=2068.6 Torr; 24 h;

1: 90 percent / acetonitrile / 3 h / Heating 2: 74.5 percent / NaH / acetonitrile 3: 76.5 percent / NH3 / methanol / 48 h / Ambient temperature 4: 97 percent / pyridine / 4 h / Ambient temperature 5: 56 percent / KF, N,O-bis(trimethylsilyl)acetamide / 18-crown-6 ether / acetonitrile / 12 h / Heating 6: 82 percent / NH3 / methanol / 12 h / Ambient temperature 7: 75 percent / NH4OH, H2O2 / dioxane; methanol; H2O / 12 h / Ambient temperature View Scheme

1: 74.5 percent / NaH / acetonitrile 2: 76.5 percent / NH3 / methanol / 48 h / Ambient temperature 3: 97 percent / pyridine / 4 h / Ambient temperature 4: 56 percent / KF, N,O-bis(trimethylsilyl)acetamide / 18-crown-6 ether / acetonitrile / 12 h / Heating 5: 82 percent / NH3 / methanol / 12 h / Ambient temperature 6: 75 percent / NH4OH, H2O2 / dioxane; methanol; H2O / 12 h / Ambient temperature View Scheme

1: 64 percent / Et3N / methanol / 3 h / Ambient temperature 2: 66 percent / 30percent H2O2, NH3, / methanol / 5.5 h / Ambient temperature 3: 56 percent / thiourea / propan-1-ol / 6.5 h / Heating 4: 1.) conc. NH3, 2.) Raney nickel / 1.) H2O, dioxane, heating, 2.) H2O, dioxane, reflux, 135 min View Scheme

1: 71 percent / Et3N / methanol / 1 h / Ambient temperature 2: 56 percent / thiourea / propan-1-ol / 6.5 h / Heating 3: 1.) conc. NH3, 2.) Raney nickel / 1.) H2O, dioxane, heating, 2.) H2O, dioxane, reflux, 135 min View Scheme

1: 66 percent / 30percent H2O2, NH3, / methanol / 5.5 h / Ambient temperature 2: 56 percent / thiourea / propan-1-ol / 6.5 h / Heating 3: 1.) conc. NH3, 2.) Raney nickel / 1.) H2O, dioxane, heating, 2.) H2O, dioxane, reflux, 135 min View Scheme

1: 56 percent / thiourea / propan-1-ol / 6.5 h / Heating 2: 1.) conc. NH3, 2.) Raney nickel / 1.) H2O, dioxane, heating, 2.) H2O, dioxane, reflux, 135 min View Scheme

ammonium hydroxide; nickel 1.) H2O, dioxane, heating, 2.) H2O, dioxane, reflux, 135 min; Yield given. Multistep reaction;

1: 52 percent / pyridine / 10 h / 110 °C 2: 61 percent / 1N NaOH / methanol / 5 h / 70 °C View Scheme