1: 80 percent / isopropanol, Raney nickel / 0.33 h / Heating 2: 1.) conc. H2SO4, NaNO2, 2.) EtOH, Cu / 1.) H2O, 0-5 deg C, 3 h, 2.) 30 deg C 3: 72 percent / pyridine / 1.) 0 deg, 4 h, 2.) room temperature, overnight 4: 90 percent / triethyl ammonium iodide / 1.5 h / Heating 5: 90 percent / H2, Et3N / 10percent Pd/C / ethyl acetate / 760 Torr 6: 87 percent / 0.5percent NaOMe / methanol / 24 h / Ambient temperature 7: 80 percent / 92percent aq. hydrazine / ethanol / 0.75 h / Heating View Scheme

1: 0.30 g / 2,6-collidine / Ambient temperature 2: Jones reagent / acetic acid View Scheme