nickel in ethanol; water 24 h; Heating;

1: 86 percent / 4-(dimethylamino)pyridine / 96 h / Ambient temperature 2: 38 percent / Et4N(+)*Cl(-), N,N-dimethylaniline, POCl3 / acetonitrile / 0.17 h / Heating 3: 86 percent / thiourea / propan-2-ol / 18 h / Heating 4: 73 percent / conc. NH4OH / methanol / 24 h / Ambient temperature 5: 38 percent / Raney Ni / H2O; ethanol / 24 h / Heating View Scheme

1: 38 percent / Et4N(+)*Cl(-), N,N-dimethylaniline, POCl3 / acetonitrile / 0.17 h / Heating 2: 86 percent / thiourea / propan-2-ol / 18 h / Heating 3: 73 percent / conc. NH4OH / methanol / 24 h / Ambient temperature 4: 38 percent / Raney Ni / H2O; ethanol / 24 h / Heating View Scheme

1: 73 percent / conc. NH4OH / methanol / 24 h / Ambient temperature 2: 38 percent / Raney Ni / H2O; ethanol / 24 h / Heating View Scheme

1: 86 percent / thiourea / propan-2-ol / 18 h / Heating 2: 73 percent / conc. NH4OH / methanol / 24 h / Ambient temperature 3: 38 percent / Raney Ni / H2O; ethanol / 24 h / Heating View Scheme

boron trichloride in dichloromethane 1.) -78 deg C, 3 h; 2.) r.t., 1 h;

1: 98 percent / 5percent Pd/C, H2, anhydrous sodium acetate / ethanol / 18 h / 2068.6 Torr / Ambient temperature 2: 70 percent / 1N BCl3 / CH2Cl2 / 1.) -78 deg C, 3 h; 2.) r.t., 1 h View Scheme