hydrazine hydrate in ethanol 0.5 h; Heating;

hydrogen bromide in acetic acid 1.5 h; Ambient temperature;

ammonia in tetrahydrofuran 5 h; Ambient temperature;

1: 1.) NaH / 1.) DMF, oil, 2-5 deg C, 15 min, 2.) DMF, oil, 2-5 deg C, 2 h 2: 97 percent / 20percent HBr / acetic acid / 1 h / Ambient temperature 3: 93.5 percent / dimethylformamide / 3 h / Ambient temperature 4: 90 percent / NH2NH2*H2O / ethanol / 0.5 h / Heating View Scheme

1: 97 percent / 20percent HBr / acetic acid / 1 h / Ambient temperature 2: 93.5 percent / dimethylformamide / 3 h / Ambient temperature 3: 90 percent / NH2NH2*H2O / ethanol / 0.5 h / Heating View Scheme

1: 93.5 percent / dimethylformamide / 3 h / Ambient temperature 2: 90 percent / NH2NH2*H2O / ethanol / 0.5 h / Heating View Scheme

1: 93.7 percent / benzene / 1 h / 70 - 80 °C 2: 90 percent / NH2NH2*H2O / ethanol / Heating View Scheme

1: 1.) HMPA, SOCl2 / 1.) CH3CN, -18 deg C, 30 min, 2.) CH3CN, -20 deg C, overnight 2: 98.5 percent / Jones reagent / acetone 3: 68 percent / HBr / acetic acid / 1.5 h / Ambient temperature View Scheme

1: 91.5 percent / KI / acetone / 1 h / Heating 2: 98 percent / dimethylformamide / 3 h / Ambient temperature 3: 90 percent / NH2NH2*H2O / ethanol / 0.5 h / Heating View Scheme

1: 1.) NaH / 1.) DMF, RT, 1.5 h, 2.) DMF, RT, overnight 2: 98.5 percent / 86percent KOH / ethanol / 2 h / Heating 3: 1.) SOCl2, 2.) NH3 (gas) / 1.) reflux, 3 h, 2.) THF, RT, 3 h 4: LiAlH4 / diethyl ether / a) RT, 10.5 h, b) reflux, 4 h 5: 1.) SOCl2, HMPA, 2.) Et3N / 1.) -5 deg C, 10 min, 2.) Et2O, RT, overnight 6: 37.2 percent / CrO3 / acetic acid; H2O / Ambient temperature 7: 68 percent / HBr / acetic acid / 1.5 h / Ambient temperature View Scheme