1: 100 percent / hydrazine hydrate / ethanol / 1 h / Ambient temperature 2: 63 percent / lead dioxide / H2O; toluene / 15 h 3: hydroxylamine hydrochloride, KOH / ethanol; methanol / 1.) 0 deg C, 30 min; 2.) r.t., 1 h 4: 21 percent / 98percent hydrazine hydrate / 10percent Pd/C / ethanol / 2 h / 65 °C View Scheme

1: 63 percent / lead dioxide / H2O; toluene / 15 h 2: hydroxylamine hydrochloride, KOH / ethanol; methanol / 1.) 0 deg C, 30 min; 2.) r.t., 1 h 3: 21 percent / 98percent hydrazine hydrate / 10percent Pd/C / ethanol / 2 h / 65 °C View Scheme

1: 86 percent / POCl3, N,N-dimethylaniline / 2 h / Heating 2: 100 percent / hydrazine hydrate / ethanol / 1 h / Ambient temperature 3: 63 percent / lead dioxide / H2O; toluene / 15 h 4: hydroxylamine hydrochloride, KOH / ethanol; methanol / 1.) 0 deg C, 30 min; 2.) r.t., 1 h 5: 21 percent / 98percent hydrazine hydrate / 10percent Pd/C / ethanol / 2 h / 65 °C View Scheme

hydrazine hydrate; palladium on activated charcoal 1.) ethanol, 65 deg C, 2 h; 2.) ethanol, r.t., 45 min; Yield given. Multistep reaction. Yields of byproduct given;

water; sodium carbonate

Yield given. Yields of byproduct given;

1: C5H5N 2: HNO3, AcOH 3: H2SO4 4: NaH View Scheme

1: C5H5N 2: HNO3, AcOH 3: H2SO4 4: NaH 5: 1.) Fe-HCl, 2.) base View Scheme