1: 86 percent / H2 / 10 percent Rh/C / ethanol / 3 h / 1500.1 Torr 2: 73 percent / p-CH3C6H4SO3H / toluene / 4 h / Heating 3: 95 percent / 10 percent Pd/C / tetrahydrofuran / 5 h / 1500.1 Torr 4: 66 percent / NaOH / methanol / 4 h / Heating 5: 1,) SOCl2, 2.) conc. NH3 / 1.) room temp., 15 h, 2.) room temp., 15 h View Scheme

1: 95 percent / 10 percent Pd/C / tetrahydrofuran / 5 h / 1500.1 Torr 2: 66 percent / NaOH / methanol / 4 h / Heating 3: 1,) SOCl2, 2.) conc. NH3 / 1.) room temp., 15 h, 2.) room temp., 15 h View Scheme

1: 66 percent / NaOH / methanol / 4 h / Heating 2: 1,) SOCl2, 2.) conc. NH3 / 1.) room temp., 15 h, 2.) room temp., 15 h View Scheme

ammonium hydroxide; thionyl chloride 1.) room temp., 15 h, 2.) room temp., 15 h; Yield given. Multistep reaction;