1: dimethylsulfoxide 2: pyridine / Heating 3: H2, glacial AcOH / 20percent Pd(OH)2/C View Scheme

1: 2.) KHCO3 / 1.) pyridine, 80 deg C, 16 h, 2.) N,N-dimethylformamide, room temperature, 18 h 2: 60 percent / 24 h / 160 °C 3: H2 / 20percent Pd(OH)2-C / acetic acid; methanol / Ambient temperature; atmospheric pressure 4: 88 percent / hydrogen chloride / propan-2-ol / 2 h / 0 °C View Scheme