1: 86 percent / H2; HClO4 / Pd/C / ethanol / 20 °C / atmospheric pressure 2: 90 percent / pyridine 3: 85 percent / chlorosulfonic acid / 1 h / 0 °C 4: 79 percent / aq. ammonia / tetrahydrofuran / 1 h / 20 °C 5: 91 percent / KOH / methanol 6: 88 percent / pyridine / 2 h / 20 °C 7: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 8: H2 / Pd/C / ethanol / 1 h / 20 °C 9: ethanol / 1 h / 20 °C 10: 2.30 g / H2 / ethanol / 2 h View Scheme

1: 86 percent / H2; HClO4 / Pd/C / ethanol / 20 °C / atmospheric pressure 2: 90 percent / pyridine 3: 85 percent / chlorosulfonic acid / 1 h / 0 °C 4: 79 percent / aq. ammonia / tetrahydrofuran / 1 h / 20 °C 5: 91 percent / KOH / methanol 6: 88 percent / pyridine / 2 h / 20 °C 7: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 8: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme