hydrogenchloride; sodium nitrite in water 1) 0 deg C, 10 min, 2) r.t., 30 min;

1: 79 percent / NaOAc, gl. AcOH / Heating 2: 86 percent / H2 / 10percent Pd/C / methanol / 760 Torr / Ambient temperature 3: 95 percent / NaNO2, 0.1N aq. HCl / H2O / 1) 0 deg C, 10 min, 2) r.t., 30 min View Scheme

1: 79 percent / NaOAc, gl. AcOH / Heating 2: 86 percent / H2 / 10percent Pd/C / methanol / 760 Torr / Ambient temperature 3: 95 percent / NaNO2, 0.1N aq. HCl / H2O / 1) 0 deg C, 10 min, 2) r.t., 30 min View Scheme

1: 86 percent / H2 / 10percent Pd/C / methanol / 760 Torr / Ambient temperature 2: 95 percent / NaNO2, 0.1N aq. HCl / H2O / 1) 0 deg C, 10 min, 2) r.t., 30 min View Scheme