potassium hydroxide; hydrazine hydrate in ethylene glycol 1.) reflux, 1 h, 2.) reflux, 1 h;

1: 81.53 percent / powdered potassium hydroxide, hydrazine hydrate / ethane-1,2-diol / 1.) reflux, 1 h, 2.) reflux, 1 h 2: thionyl chloride, dimethylformamide 3: triethylamine / CHCl3 / 3 h / 35 °C 4: 20percent HCl / CHCl3 / 5 h / Heating 5: NaOH / ethanol 6: potassium carbonate / acetone / Heating 7: BF3*O(C2H5)2 / CHCl3 / 36 h / Ambient temperature 8: H2 / Raney nickel / ethanol / 9 h / Heating 9: 95 percent / lithium aluminium hydride / tetrahydrofuran / 1.) -10 deg C to room temperature, 1 h, 2.) room temperature, 4 h View Scheme

1: 81.53 percent / powdered potassium hydroxide, hydrazine hydrate / ethane-1,2-diol / 1.) reflux, 1 h, 2.) reflux, 1 h 2: thionyl chloride, dimethylformamide 3: triethylamine / CHCl3 / 3 h / 35 °C 4: 20percent HCl / CHCl3 / 5 h / Heating 5: NaOH / ethanol 6: potassium carbonate / acetone / Heating 7: BF3*O(C2H5)2 / CHCl3 / 36 h / Ambient temperature 8: H2 / Raney nickel / ethanol / 9 h / Heating View Scheme

1: 81.53 percent / powdered potassium hydroxide, hydrazine hydrate / ethane-1,2-diol / 1.) reflux, 1 h, 2.) reflux, 1 h 2: 0 °C View Scheme