in 4-benzyloxy-5-ethoxyindole

10 palladium on carbon; hydrogen; acetic acid in ethanol T=20°C; P=750.075 Torr; 8 h;

sodium hydroxide; sodium dithionite in N,N-dimethyl-formamide T=5°C; 0.333333 h;

1: 76 percent / sodium acetate / 1.5 h / 70 °C 2: 70 percent / KF, 18-crown-6, N-methylmorpholine / 21 h / 10 °C 3: 96 percent / silica gel, reduced iron powder, glacial AcOH / toluene / 0.5 h / 90 °C 4: 54 percent / Na2S2O4, aq. NaOH / dimethylformamide / 0.33 h / 5 °C View Scheme

1: 95 percent / boron tribromide / CH2Cl2 / Ambient temperature 2: 76 percent / sodium acetate / 1.5 h / 70 °C 3: 70 percent / KF, 18-crown-6, N-methylmorpholine / 21 h / 10 °C 4: 96 percent / silica gel, reduced iron powder, glacial AcOH / toluene / 0.5 h / 90 °C 5: 54 percent / Na2S2O4, aq. NaOH / dimethylformamide / 0.33 h / 5 °C View Scheme

1: 49 percent / HNO3 / acetic acid / 0.75 h / Ambient temperature 2: 95 percent / boron tribromide / CH2Cl2 / Ambient temperature 3: 76 percent / sodium acetate / 1.5 h / 70 °C 4: 70 percent / KF, 18-crown-6, N-methylmorpholine / 21 h / 10 °C 5: 96 percent / silica gel, reduced iron powder, glacial AcOH / toluene / 0.5 h / 90 °C 6: 54 percent / Na2S2O4, aq. NaOH / dimethylformamide / 0.33 h / 5 °C View Scheme