hydrazine hydrate in ethanol 3 h; Heating;

1: 71 percent / xylene / 72 h / Heating 2: 98 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 3: 82.5 percent / triphenyl phosphine, diethyl azodicarboxylate / tetrahydrofuran / 1 h / Ambient temperature 4: 51 percent / hydrazine hydrate / ethanol / 3 h / Heating View Scheme

1: 98 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 2: 82.5 percent / triphenyl phosphine, diethyl azodicarboxylate / tetrahydrofuran / 1 h / Ambient temperature 3: 51 percent / hydrazine hydrate / ethanol / 3 h / Heating View Scheme

1: aq. KOH, CH2N2 / diethyl ether; various solvent(s) / 0.75 h / Ambient temperature 2: glacial AcOH / 0.5 h / Ambient temperature 3: 71 percent / xylene / 72 h / Heating 4: 98 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 5: 82.5 percent / triphenyl phosphine, diethyl azodicarboxylate / tetrahydrofuran / 1 h / Ambient temperature 6: 51 percent / hydrazine hydrate / ethanol / 3 h / Heating View Scheme

1: 82.5 percent / triphenyl phosphine, diethyl azodicarboxylate / tetrahydrofuran / 1 h / Ambient temperature 2: 51 percent / hydrazine hydrate / ethanol / 3 h / Heating View Scheme