sodium hydroxide in methanol 0.25 h; Ambient temperature;

1: 73 percent / conc. H2SO4, conc. HNO3 / 1.5 h / Ambient temperature 2: 79 percent / Et3N / toluene / 6 h / Heating 3: 74 percent / H2 / 5percent Pd/C / ethyl acetate / 3 h / 2068.6 Torr 4: 1.) aq. HCl, NaNO2, 2.) NaN3 / 1.) from 0 deg C to 5 deg C, 1 h 5: 47 percent / 10percent aq. NaOH / methanol / 0.25 h / Ambient temperature View Scheme

1: 79 percent / Et3N / toluene / 6 h / Heating 2: 74 percent / H2 / 5percent Pd/C / ethyl acetate / 3 h / 2068.6 Torr 3: 1.) aq. HCl, NaNO2, 2.) NaN3 / 1.) from 0 deg C to 5 deg C, 1 h 4: 47 percent / 10percent aq. NaOH / methanol / 0.25 h / Ambient temperature View Scheme