1: 1.04 g / SOCl2; pyridine / 20 °C 2: 78 percent / NaN3 / dimethylformamide / 3 h / 80 °C 3: 91 percent / H2 / Pd/C / ethanol / 6 h / 1292.87 Torr 4: 52 percent / pyridine / 1-methyl-pyrrolidin-2-one / 5 h / 140 °C 5: 90 percent / conc. HCl / 5 h / 20 °C 6: 82 percent / NH4F / methanol / Heating View Scheme

1.1: SOCl2 / pyridine 2.1: RuCl3; NaIO4 / acetonitrile; CCl4; H2O 3.1: DBU / acetonitrile / 0.5 h / 20 °C 3.2: acetonitrile / 2 h / 75 °C 3.3: silica gel / CH2Cl2; methanol 4.1: HCl / methanol; H2O / 20 h / 65 °C View Scheme