hydrogen; palladium on activated charcoal in perchloric acid; ethanol Ambient temperature;

potassium hydroxide; hydrazine hydrate in water; ethylene glycol 120 degC, 1 h then 190-195 degC, 3 h;

nickel in ethanol 6 h; Heating;

hydrogen; nickel 1.) boiling 70percent aq. EtOH, 6h, 2.) 1 atm, room temp., 3.5 h; Yield given. Multistep reaction;

1: 82 percent / Hg(OAc)2, EDTA 2: 89 percent / HClO4, H2 / Pd / ethanol / 6 h / 760 Torr / Ambient temperature 3: 1.) NH2NH2, 2.) KOH View Scheme

1: 98 percent / HCL aq. / 2 h / 40 °C 2: 82 percent / Hg(OAc)2, EDTA 3: 89 percent / HClO4, H2 / Pd / ethanol / 6 h / 760 Torr / Ambient temperature 4: 1.) NH2NH2, 2.) KOH View Scheme

1: 89 percent / HClO4, H2 / Pd / ethanol / 6 h / 760 Torr / Ambient temperature 2: 1.) NH2NH2, 2.) KOH View Scheme

1: 1.) hydrogen, 2.) NaBH4 / 1.) 50percent aq. EtOH, Adams catalyst (PtO2*H2O), 1 atm, room temp., 18 h 2: 98 percent / HCL aq. / 2 h / 40 °C 3: 82 percent / Hg(OAc)2, EDTA 4: 89 percent / HClO4, H2 / Pd / ethanol / 6 h / 760 Torr / Ambient temperature 5: 1.) NH2NH2, 2.) KOH View Scheme

1: 99 percent / benzene / 5 h / Ambient temperature 2: 1.) H2; 2.) NaBH4 / 1.) Adams catalyst / 1.) ethanol/water, 18 h, room temperature; 2.) ethanol/water, room temperature 3: 98 percent / 1N HCl / H2O / 2 h / 40 °C 4: 82 percent / Hg(OAc)2-EDTA / aq. acetic acid / Heating 5: 89 percent / H2, 70percent HClO4 / 10percent Pd-C / ethanol; H2O / 6 h / Ambient temperature 6: 84 percent / hydrazine hydrate, KOH / H2O; ethane-1,2-diol / 120 degC, 1 h then 190-195 degC, 3 h View Scheme

1: 99 percent / benzene / 5 h / Ambient temperature 2: 1.) H2; 2.) NaBH4 / 1.) Adams catalyst / 1.) ethanol/water, 18 h, room temperature; 2.) ethanol/water, room temperature 3: 98 percent / 1N HCl / H2O / 2 h / 40 °C 4: 82 percent / Hg(OAc)2-EDTA / aq. acetic acid / Heating 5: 89 percent / H2, 70percent HClO4 / 10percent Pd-C / ethanol; H2O / 6 h / Ambient temperature 6: 84 percent / hydrazine hydrate, KOH / H2O; ethane-1,2-diol / 120 degC, 1 h then 190-195 degC, 3 h View Scheme