hydrogen; palladium on activated charcoal in ethanol Yield given;

1: conc. H2SO4, HNO3 / 2 h / -10 - 0 °C 2: H2 / 10percent Pd/C / ethanol View Scheme

1: 48 percent / Triton B / dioxane; methanol / 15 h / Heating 2: NaOH / aq. ethanol; tetrahydrofuran / 3 h 3: polyphosphoric acid / 3 h / 130 - 140 °C 4: conc. H2SO4, HNO3 / 2 h / -10 - 0 °C 5: H2 / 10percent Pd/C / ethanol View Scheme

1: 74 percent / NaNH2 / benzene / 1 h / 80 °C 2: 48 percent / Triton B / dioxane; methanol / 15 h / Heating 3: NaOH / aq. ethanol; tetrahydrofuran / 3 h 4: polyphosphoric acid / 3 h / 130 - 140 °C 5: conc. H2SO4, HNO3 / 2 h / -10 - 0 °C 6: H2 / 10percent Pd/C / ethanol View Scheme