hydrogen; acetic acid; nickel T=20 - 23°C; P=724.007 - 775.7 Torr; 14 h;

hydrogen; acetic acid; nickel T=25°C; 17 h;

1: 85 percent / NaOEt / ethanol / 1 h / Ambient temperature 2: 1.) NaNO2, HCl, 2.) HCl, H2O / 1.) water, 2.5 h, 2.) 1 h 3: 88 percent / MgO, H2 / 10percent Pd/C / dioxane / 2585.7 Torr 4: 84 percent / H2 / Raney Ni / acetic acid / 2585.7 Torr 5: 89 percent / NaNO2, AcOH, Ac2O / 2 h / Ambient temperature 6: 90 percent / Heating 7: 83 percent / BCl3 / CH2Cl2 / a) -78 deg C, 3 h, b) RT, overnight 8: 80 percent / pyridine / 48 h / Ambient temperature 9: p-TsOH, hexamethyldisilazane, NH3 / 120 h / 155 - 160 °C 10: 50percent aq. MeOH / 4 h / Heating 11: HBr / dioxane / 20 h 12: N,N-dimethyl-acetamide / 72 h / Ambient temperature View Scheme

1: 1.) NaNO2, HCl, 2.) HCl, H2O / 1.) water, 2.5 h, 2.) 1 h 2: 88 percent / MgO, H2 / 10percent Pd/C / dioxane / 2585.7 Torr 3: 84 percent / H2 / Raney Ni / acetic acid / 2585.7 Torr 4: 89 percent / NaNO2, AcOH, Ac2O / 2 h / Ambient temperature 5: 90 percent / Heating 6: 83 percent / BCl3 / CH2Cl2 / a) -78 deg C, 3 h, b) RT, overnight 7: 80 percent / pyridine / 48 h / Ambient temperature 8: p-TsOH, hexamethyldisilazane, NH3 / 120 h / 155 - 160 °C 9: 50percent aq. MeOH / 4 h / Heating 10: HBr / dioxane / 20 h 11: N,N-dimethyl-acetamide / 72 h / Ambient temperature View Scheme

1: 84 percent / H2 / Raney Ni / acetic acid / 2585.7 Torr 2: 89 percent / NaNO2, AcOH, Ac2O / 2 h / Ambient temperature 3: 90 percent / Heating 4: 83 percent / BCl3 / CH2Cl2 / a) -78 deg C, 3 h, b) RT, overnight 5: 80 percent / pyridine / 48 h / Ambient temperature 6: p-TsOH, hexamethyldisilazane, NH3 / 120 h / 155 - 160 °C 7: 50percent aq. MeOH / 4 h / Heating 8: HBr / dioxane / 20 h 9: N,N-dimethyl-acetamide / 72 h / Ambient temperature View Scheme

1: 88 percent / MgO, H2 / 10percent Pd/C / dioxane / 2585.7 Torr 2: 84 percent / H2 / Raney Ni / acetic acid / 2585.7 Torr 3: 89 percent / NaNO2, AcOH, Ac2O / 2 h / Ambient temperature 4: 90 percent / Heating 5: 83 percent / BCl3 / CH2Cl2 / a) -78 deg C, 3 h, b) RT, overnight 6: 80 percent / pyridine / 48 h / Ambient temperature 7: p-TsOH, hexamethyldisilazane, NH3 / 120 h / 155 - 160 °C 8: 50percent aq. MeOH / 4 h / Heating 9: HBr / dioxane / 20 h 10: N,N-dimethyl-acetamide / 72 h / Ambient temperature View Scheme

1: 276 mg / SOCl2 / CHCl3; dimethylformamide / Heating 2: 88 percent / MgO, H2 / 10percent Pd/C / dioxane / 2585.7 Torr 3: 84 percent / H2 / Raney Ni / acetic acid / 2585.7 Torr 4: 89 percent / NaNO2, AcOH, Ac2O / 2 h / Ambient temperature 5: 90 percent / Heating 6: 83 percent / BCl3 / CH2Cl2 / a) -78 deg C, 3 h, b) RT, overnight 7: 80 percent / pyridine / 48 h / Ambient temperature 8: p-TsOH, hexamethyldisilazane, NH3 / 120 h / 155 - 160 °C 9: 50percent aq. MeOH / 4 h / Heating 10: HBr / dioxane / 20 h 11: N,N-dimethyl-acetamide / 72 h / Ambient temperature View Scheme

in AcOH--H2 O; ethanol

1: HBr / dioxane / 20 h 2: N,N-dimethyl-acetamide / 72 h / Ambient temperature View Scheme

1: 80 percent / pyridine / 48 h / Ambient temperature 2: p-TsOH, hexamethyldisilazane, NH3 / 120 h / 155 - 160 °C 3: 50percent aq. MeOH / 4 h / Heating 4: HBr / dioxane / 20 h 5: N,N-dimethyl-acetamide / 72 h / Ambient temperature View Scheme