hydrogen; palladium on activated charcoal in ethanol T=20°C; P=760 Torr; 4 h; Yields of byproduct given;

1: H2, thriethylamine / Pd/C / ethyl acetate / 76000 Torr / Ambient temperature 2: aq. perchloric acid / 1 h 3: H2, triethylamine / Pd/C / ethyl acetate / 20 h / 76000 Torr / Ambient temperature 4: 1.) KOH, 2.) 2M HCl / 2.) 50 deg C View Scheme

1: H2, thriethylamine / Pd/C / ethyl acetate / 76000 Torr / Ambient temperature 2: aq. perchloric acid / 1 h 3: H2, triethylamine / Pd/C / ethyl acetate / 20 h / 76000 Torr / Ambient temperature 4: 1.) KOH, 2.) 2M HCl / 2.) 50 deg C 5: 83 percent / pyridine / 0 °C View Scheme