hydrogen; palladium on activated charcoal in ethanol; ethyl acetate P=760 Torr; 5 h; Yield given;

1: 70percent aq. HNO3, H2SO4 / 0.08 h / 0 °C 2: H2 / 10percent Pd/C / ethyl acetate; ethanol / 5 h / 760 Torr View Scheme

1: 85 percent / K2CO3 / dimethylformamide / Ambient temperature 2: 65 percent / Pd(OAc)2, NaHCO3 / dimethylformamide / 90 °C 3: 70percent aq. HNO3, H2SO4 / 0.08 h / 0 °C 4: H2 / 10percent Pd/C / ethyl acetate; ethanol / 5 h / 760 Torr View Scheme

1: 65 percent / Pd(OAc)2, NaHCO3 / dimethylformamide / 90 °C 2: 70percent aq. HNO3, H2SO4 / 0.08 h / 0 °C 3: H2 / 10percent Pd/C / ethyl acetate; ethanol / 5 h / 760 Torr View Scheme