sodium in ethanol 1.) room temp., 1 h; 2.) reflux, 1 h; Yield given;

1: 92 percent / 98percent hydrazine hydrate / ethanol / 20 h / Heating 2: 70 percent / potassium permanganate, potassium hydroxide / pyridine; H2O / 7 h / Heating 3: 30 g / HCl / 16 h / Heating 4: LiAlH4 / tetrahydrofuran / 3 h / Heating 5: 95 percent / hydrogen bromide / acetic acid / 21 h / 20 °C 6: sodium / ethanol / 1.) room temp., 1 h; 2.) reflux, 1 h View Scheme

1: 95 percent / hydrogen bromide / acetic acid / 21 h / 20 °C 2: sodium / ethanol / 1.) room temp., 1 h; 2.) reflux, 1 h View Scheme

1: 70 percent / potassium permanganate, potassium hydroxide / pyridine; H2O / 7 h / Heating 2: 30 g / HCl / 16 h / Heating 3: LiAlH4 / tetrahydrofuran / 3 h / Heating 4: 95 percent / hydrogen bromide / acetic acid / 21 h / 20 °C 5: sodium / ethanol / 1.) room temp., 1 h; 2.) reflux, 1 h View Scheme

1: 30 g / HCl / 16 h / Heating 2: LiAlH4 / tetrahydrofuran / 3 h / Heating 3: 95 percent / hydrogen bromide / acetic acid / 21 h / 20 °C 4: sodium / ethanol / 1.) room temp., 1 h; 2.) reflux, 1 h View Scheme

1: LiAlH4 / tetrahydrofuran / 3 h / Heating 2: 95 percent / hydrogen bromide / acetic acid / 21 h / 20 °C 3: sodium / ethanol / 1.) room temp., 1 h; 2.) reflux, 1 h View Scheme