lithium aluminium tetrahydride in tetrahydrofuran 1.5 h; Heating;

1: 60 percent / pyridine / 1 h / Ambient temperature 2: 40 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating View Scheme

1: 77 percent / aq. AcOH / 0.5 h / Heating 2: 60 percent / pyridine / 1 h / Ambient temperature 3: 40 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating View Scheme

1: 77 percent / aq. HCl, NaNO2 / 0.33 h / 0 °C 2: 77 percent / aq. AcOH / 0.5 h / Heating 3: 60 percent / pyridine / 1 h / Ambient temperature 4: 40 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating View Scheme

1: 80 percent / 85percent hydrazine hydrate / ethanol / 6 h / Heating 2: 77 percent / aq. HCl, NaNO2 / 0.33 h / 0 °C 3: 77 percent / aq. AcOH / 0.5 h / Heating 4: 60 percent / pyridine / 1 h / Ambient temperature 5: 40 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating View Scheme

1.1: hydrazine hydrate / pentan-1-ol / 7 h / 150 °C 2.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 °C 3.1: o-xylene / 1 h / 160 °C 4.1: water; potassium hydroxide / ethanol / 2 h / Reflux 5.1: pyridine / 5 h / 20 °C 5.2: 1 h / 20 °C / Saturated solution 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Reflux 6.2: 2 h / 20 °C View Scheme

1.1: trichloroisocyanuric acid; triethylamine / N,N-dimethyl-formamide / 2 h / -20 - 0 °C 2.1: hydrazine hydrate / pentan-1-ol / 7 h / 150 °C 3.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 °C 4.1: o-xylene / 1 h / 160 °C 5.1: water; potassium hydroxide / ethanol / 2 h / Reflux 6.1: pyridine / 5 h / 20 °C 6.2: 1 h / 20 °C / Saturated solution 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Reflux 7.2: 2 h / 20 °C View Scheme

1.1: sodium hydroxide / water / 5 h / 20 °C / Reflux 1.2: pH 5 2.1: thionyl chloride / 24 h / -10 °C / Reflux 2.2: pH 8 3.1: trichloroisocyanuric acid; triethylamine / N,N-dimethyl-formamide / 2 h / -20 - 0 °C 4.1: hydrazine hydrate / pentan-1-ol / 7 h / 150 °C 5.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 °C 6.1: o-xylene / 1 h / 160 °C 7.1: water; potassium hydroxide / ethanol / 2 h / Reflux 8.1: pyridine / 5 h / 20 °C 8.2: 1 h / 20 °C / Saturated solution 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Reflux 9.2: 2 h / 20 °C View Scheme

1.1: thionyl chloride / 24 h / -10 °C / Reflux 1.2: pH 8 2.1: trichloroisocyanuric acid; triethylamine / N,N-dimethyl-formamide / 2 h / -20 - 0 °C 3.1: hydrazine hydrate / pentan-1-ol / 7 h / 150 °C 4.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 °C 5.1: o-xylene / 1 h / 160 °C 6.1: water; potassium hydroxide / ethanol / 2 h / Reflux 7.1: pyridine / 5 h / 20 °C 7.2: 1 h / 20 °C / Saturated solution 8.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Reflux 8.2: 2 h / 20 °C View Scheme