hydrogen; triethylamine; palladium on activated charcoal in ethyl acetate P=2585.7 Torr; 3 h;

1: 96 percent / H2 / Ra-Ni / ethyl acetate / 6 h / 2327.2 Torr 3: NaNO2, 2 N aq. HCl / H2O / 1 h / 0 °C 4: LiAlH4 / tetrahydrofuran / 1 h / Heating 5: 1.) pyridinium 3-nitrobenzenesulfonic acid, 2.) AcOH / 1.) H2O, reflux, 3 h, 2.) reflux, 1 h View Scheme

1: NaNO2, 2 N aq. HCl / H2O / 1 h / 0 °C 2: LiAlH4 / tetrahydrofuran / 1 h / Heating 3: 1.) pyridinium 3-nitrobenzenesulfonic acid, 2.) AcOH / 1.) H2O, reflux, 3 h, 2.) reflux, 1 h View Scheme

1: 69 percent / tetrahydrofuran / 0.33 h / 0 °C 2: 20 percent / NaH / dioxane / Ambient temperature 3: 1.) pyridinium 3-nitrobenzenesulfonic acid, 2.) AcOH / 1.) H2O, reflux, 3 h, 2.) reflux, 1 h 4: 26 percent / H2, Et3N / 10percent Pd/C / ethyl acetate / 3 h / 2585.7 Torr View Scheme

1: 1.) pyridinium 3-nitrobenzenesulfonic acid, 2.) AcOH / 1.) H2O, reflux, 3 h, 2.) reflux, 1 h 2: 26 percent / H2, Et3N / 10percent Pd/C / ethyl acetate / 3 h / 2585.7 Torr View Scheme

1: 1.) pyridinium 3-nitrobenzenesulfonic acid, 2.) AcOH / 1.) H2O, reflux, 3 h, 2.) reflux, 1 h 2: 26 percent / H2, Et3N / 10percent Pd/C / ethyl acetate / 3 h / 2585.7 Torr View Scheme

acetic acid; pyridinium paratoluene sulfonic acid 1.) H2O, reflux, 3 h, 2.) reflux, 1 h; Multistep reaction;