sulfuric acid; diisobutylaluminium hydride in water; ethyl acetate; toluene

1: AlCl3 / CH2Cl2 / 5 h / Ambient temperature 2: 1) hydrazine hydrate, 2) KOH / 1) diethylene glycol, 130 deg C, 1 h, 2) diethylene glycol, 130 deg C, 2 h, then 160 deg C, 3 h 3: 1) TiCl4, 2) hydroxylamine hydrochloride, pyridine / 1) CH2Cl2, 0 deg C, 30 min, 2) ethanol, reflux, 2 h 4: 73 percent / acetic anhydride / 2 h / Heating 5: 2.5 g / Ni-Al alloy, 75percent formic acid / 8 h / Heating View Scheme

1: AlCl3 / CH2Cl2 / 5 h / Ambient temperature 2: 1) hydrazine hydrate, 2) KOH / 1) diethylene glycol, 130 deg C, 1 h, 2) diethylene glycol, 130 deg C, 2 h, then 160 deg C, 3 h 3: 1) TiCl4, 2) hydroxylamine hydrochloride, pyridine / 1) CH2Cl2, 0 deg C, 30 min, 2) ethanol, reflux, 2 h 4: 73 percent / acetic anhydride / 2 h / Heating 5: 2.5 g / Ni-Al alloy, 75percent formic acid / 8 h / Heating View Scheme

1: 1) hydrazine hydrate, 2) KOH / 1) diethylene glycol, 130 deg C, 1 h, 2) diethylene glycol, 130 deg C, 2 h, then 160 deg C, 3 h 2: 1) TiCl4, 2) hydroxylamine hydrochloride, pyridine / 1) CH2Cl2, 0 deg C, 30 min, 2) ethanol, reflux, 2 h 3: 73 percent / acetic anhydride / 2 h / Heating 4: 2.5 g / Ni-Al alloy, 75percent formic acid / 8 h / Heating View Scheme

1: 1) TiCl4, 2) hydroxylamine hydrochloride, pyridine / 1) CH2Cl2, 0 deg C, 30 min, 2) ethanol, reflux, 2 h 2: 73 percent / acetic anhydride / 2 h / Heating 3: 2.5 g / Ni-Al alloy, 75percent formic acid / 8 h / Heating View Scheme

1: 73 percent / acetic anhydride / 2 h / Heating 2: 2.5 g / Ni-Al alloy, 75percent formic acid / 8 h / Heating View Scheme