NaH in MeOH--H2 O; dimethyl sulfoxide

sodium in ammonia

1: 46 percent / Et3N / dimethylformamide / 16 h 2: 78 percent / hydrazine hydrate / ethanol / 16 h / Heating 3: acetone / 0.5 h / Heating 4: 82 percent / 0.2N aq. NaOH / 2 h 5: 93 percent / 7N aq. NaOH / dioxane / 6 h / Heating 6: 66 percent / hydrazine hydrate / ethanol / 16 h / Heating 7: 73 percent / Na / liquid ammonia View Scheme

1: 78 percent / hydrazine hydrate / ethanol / 16 h / Heating 2: acetone / 0.5 h / Heating 3: 82 percent / 0.2N aq. NaOH / 2 h 4: 93 percent / 7N aq. NaOH / dioxane / 6 h / Heating 5: 66 percent / hydrazine hydrate / ethanol / 16 h / Heating 6: 73 percent / Na / liquid ammonia View Scheme

1: 66 percent / hydrazine hydrate / ethanol / 16 h / Heating 2: 73 percent / Na / liquid ammonia View Scheme

1: 82 percent / 0.2N aq. NaOH / 2 h 2: 93 percent / 7N aq. NaOH / dioxane / 6 h / Heating 3: 66 percent / hydrazine hydrate / ethanol / 16 h / Heating 4: 73 percent / Na / liquid ammonia View Scheme

1: 93 percent / 7N aq. NaOH / dioxane / 6 h / Heating 2: 66 percent / hydrazine hydrate / ethanol / 16 h / Heating 3: 73 percent / Na / liquid ammonia View Scheme

1: acetone / 0.5 h / Heating 2: 82 percent / 0.2N aq. NaOH / 2 h 3: 93 percent / 7N aq. NaOH / dioxane / 6 h / Heating 4: 66 percent / hydrazine hydrate / ethanol / 16 h / Heating 5: 73 percent / Na / liquid ammonia View Scheme

1: 63 percent / dimethylaminopyridine / pyridine / 7 h / 50 °C 2: 46 percent / Et3N / dimethylformamide / 16 h 3: 78 percent / hydrazine hydrate / ethanol / 16 h / Heating 4: acetone / 0.5 h / Heating 5: 82 percent / 0.2N aq. NaOH / 2 h 6: 93 percent / 7N aq. NaOH / dioxane / 6 h / Heating 7: 66 percent / hydrazine hydrate / ethanol / 16 h / Heating 8: 73 percent / Na / liquid ammonia View Scheme

sodium hydride 1) dimethylformamide, 10 min; 2) DMF, room temperature 25 min; Yield given. Multistep reaction;