1: 75 percent / tetrakis(acetonitrile)copper(I) tetrafluoroborate / toluene / 20 h / 80 - 90 °C 2: 95 percent / H2 / Raney-Ni / ethanol / 1 h / 760 Torr View Scheme

1: 95 percent / H2 / Raney-Ni / ethanol / 1 h / 760 Torr View Scheme

1: 72 percent / hydrazine hydrate / Raney-Ni / ethanol; 1,2-dichloro-ethane / 3.5 h / 60 °C 2: 75 percent / tetrakis(acetonitrile)copper(I) tetrafluoroborate / toluene / 20 h / 80 - 90 °C 3: 95 percent / H2 / Raney-Ni / ethanol / 1 h / 760 Torr View Scheme

1: Et3N / ethanol / 4 h / Heating 2: 72 percent / hydrazine hydrate / Raney-Ni / ethanol; 1,2-dichloro-ethane / 3.5 h / 60 °C 3: 75 percent / tetrakis(acetonitrile)copper(I) tetrafluoroborate / toluene / 20 h / 80 - 90 °C 4: 95 percent / H2 / Raney-Ni / ethanol / 1 h / 760 Torr View Scheme

Multistep reaction;