1: 89 percent / NaNO2, HNO3 2: 75 percent 3: dimethylformamide / 6 h / 130 °C 4: H2 / Raney-Ni / 2896.03 Torr 5: diethyl ether / 0.5 h / 0 °C 6: NH3 / toluene 7: 1.) (CH3)2S*BH3, 2.) aq. HCl / 1.) THF, reflux, 30 min, 2.) 100 deg C, 20 min 8: pyridine / ethyl acetate / Ambient temperature View Scheme

1: 75 percent 2: dimethylformamide / 6 h / 130 °C 3: H2 / Raney-Ni / 2896.03 Torr 4: diethyl ether / 0.5 h / 0 °C 5: NH3 / toluene 6: 1.) (CH3)2S*BH3, 2.) aq. HCl / 1.) THF, reflux, 30 min, 2.) 100 deg C, 20 min 7: pyridine / ethyl acetate / Ambient temperature View Scheme

1: dimethylformamide / 6 h / 130 °C 2: H2 / Raney-Ni / 2896.03 Torr 3: diethyl ether / 0.5 h / 0 °C 4: NH3 / toluene 5: 1.) (CH3)2S*BH3, 2.) aq. HCl / 1.) THF, reflux, 30 min, 2.) 100 deg C, 20 min 6: pyridine / ethyl acetate / Ambient temperature View Scheme

1: H2 / Raney-Ni / 2896.03 Torr 2: diethyl ether / 0.5 h / 0 °C 3: NH3 / toluene 4: 1.) (CH3)2S*BH3, 2.) aq. HCl / 1.) THF, reflux, 30 min, 2.) 100 deg C, 20 min 5: pyridine / ethyl acetate / Ambient temperature View Scheme

1: diethyl ether / 0.5 h / 0 °C 2: NH3 / toluene 3: 1.) (CH3)2S*BH3, 2.) aq. HCl / 1.) THF, reflux, 30 min, 2.) 100 deg C, 20 min 4: pyridine / ethyl acetate / Ambient temperature View Scheme

1: 1.) (CH3)2S*BH3, 2.) aq. HCl / 1.) THF, reflux, 30 min, 2.) 100 deg C, 20 min 2: pyridine / ethyl acetate / Ambient temperature View Scheme

pyridine in ethyl acetate Ambient temperature; Yield given;