1: 1.) liq. NH3; 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 2 h 2: 60 percent / n-Bu3SnH, α-α'azobis-iso-butyronitrile / benzene 3: 89 percent / SOCl2 / pyridine / 0.25 h / 2 °C 4: 1.) 1percent NaOH; 2.) Na / 1.) MeOH; 2.) liq. NH3 5: pyridine 6: 92 percent / 80percent aq. NH2NH2 / sealed tube View Scheme

Multi-step reaction with 2 steps 1: 1.) liq. NH3; 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 2 h2: 60 percent / n-Bu3SnH, α-α'azobis-iso-butyronitrile / benzene  

Multi-step reaction with 3 steps 1: 1.) liq. NH3; 2.) p-TsOH*H2O / 1.) THF, -78 deg C, 2 h2: 60 percent / n-Bu3SnH, α-α'azobis-iso-butyronitrile / benzene3: 89 percent / SOCl2 / pyridine / 0.25 h / 2 °C