hydrazine hydrate; nickel in ethanol 2 h; Heating;

2: 95 percent / 20percent aq. KOH / ethanol / 48 h / Heating 3: thionyl chloride (SOCl2) / 1 h / Heating 4: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 5: 16 percent / ammonium nitrate, trifluoroacetic anhydride / acetonitrile / Ambient temperature 6: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 7: p-toluenesulfonic acid / toluene / 3 h / Heating 8: 56 percent / dichlorodicyanobenzoquinone (DDQ) / toluene / 2 h / Heating 9: 95 percent / hydrazine monohydrate / Raney Ni / ethanol / 2 h / Heating View Scheme

1: thionyl chloride (SOCl2) / 1 h / Heating 2: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 3: 16 percent / ammonium nitrate, trifluoroacetic anhydride / acetonitrile / Ambient temperature 4: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 5: p-toluenesulfonic acid / toluene / 3 h / Heating 6: 56 percent / dichlorodicyanobenzoquinone (DDQ) / toluene / 2 h / Heating 7: 95 percent / hydrazine monohydrate / Raney Ni / ethanol / 2 h / Heating View Scheme

1: 16 percent / ammonium nitrate, trifluoroacetic anhydride / acetonitrile / Ambient temperature 2: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 3: p-toluenesulfonic acid / toluene / 3 h / Heating 4: 56 percent / dichlorodicyanobenzoquinone (DDQ) / toluene / 2 h / Heating 5: 95 percent / hydrazine monohydrate / Raney Ni / ethanol / 2 h / Heating View Scheme

1: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 2: 16 percent / ammonium nitrate, trifluoroacetic anhydride / acetonitrile / Ambient temperature 3: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 4: p-toluenesulfonic acid / toluene / 3 h / Heating 5: 56 percent / dichlorodicyanobenzoquinone (DDQ) / toluene / 2 h / Heating 6: 95 percent / hydrazine monohydrate / Raney Ni / ethanol / 2 h / Heating View Scheme

1: 56 percent / dichlorodicyanobenzoquinone (DDQ) / toluene / 2 h / Heating 2: 95 percent / hydrazine monohydrate / Raney Ni / ethanol / 2 h / Heating View Scheme

1: 95 percent / 20percent aq. KOH / ethanol / 48 h / Heating 2: thionyl chloride (SOCl2) / 1 h / Heating 3: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 4: 16 percent / ammonium nitrate, trifluoroacetic anhydride / acetonitrile / Ambient temperature 5: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 6: p-toluenesulfonic acid / toluene / 3 h / Heating 7: 56 percent / dichlorodicyanobenzoquinone (DDQ) / toluene / 2 h / Heating 8: 95 percent / hydrazine monohydrate / Raney Ni / ethanol / 2 h / Heating View Scheme

1: Cu / 200 - 250 °C 2: H2, aq. HClO4 / Pd-C 3: (i) BCl3, (ii) AlCl3 View Scheme

1: Cu / 200 - 250 °C 2: H2, aq. HClO4 / Pd-C 3: (i) BCl3, (ii) AlCl3 View Scheme

1: H2, aq. HClO4 / Pd-C 2: (i) BCl3, (ii) AlCl3 View Scheme