pyridine; ammonium hydroxide; triphenylphosphine

hydrogen; palladium on activated charcoal in ethanol T=24°C; 1.5 h;

1: thionyl chloride / CHCl3; dimethylformamide / 6 h / Heating 2: 31 percent / NH3 / methanol / 144 h / Ambient temperature 3: 65 percent / H2 / 10percent Pd/C / methanol / 2 h / 2585.7 Torr View Scheme

1: pyridine / 24 h / 4 °C 2: thionyl chloride / CHCl3; dimethylformamide / 6 h / Heating 3: 31 percent / NH3 / methanol / 144 h / Ambient temperature 4: 65 percent / H2 / 10percent Pd/C / methanol / 2 h / 2585.7 Torr View Scheme

1: 70 percent / 80percent acetic acid / 0.33 h / Heating 2: pyridine / 24 h / 4 °C 3: thionyl chloride / CHCl3; dimethylformamide / 6 h / Heating 4: 31 percent / NH3 / methanol / 144 h / Ambient temperature 5: 65 percent / H2 / 10percent Pd/C / methanol / 2 h / 2585.7 Torr View Scheme

1: 31 percent / NH3 / methanol / 144 h / Ambient temperature 2: 65 percent / H2 / 10percent Pd/C / methanol / 2 h / 2585.7 Torr View Scheme

1: 93 percent / pyridine / 24 h / 4 °C 2: 88 percent / 1N NaOH / ethanol; H2O / 4 h / Heating 3: 91 percent / pyridine / 24 h / Ambient temperature 4: 86 percent / LiN3 / dimethylformamide / 2 h / 85 °C 5: 70 percent / 80percent acetic acid / 0.33 h / Heating 6: pyridine / 24 h / 4 °C 7: thionyl chloride / CHCl3; dimethylformamide / 6 h / Heating 8: 31 percent / NH3 / methanol / 144 h / Ambient temperature 9: 65 percent / H2 / 10percent Pd/C / methanol / 2 h / 2585.7 Torr View Scheme

1: 86 percent / LiN3 / dimethylformamide / 2 h / 85 °C 2: 70 percent / 80percent acetic acid / 0.33 h / Heating 3: pyridine / 24 h / 4 °C 4: thionyl chloride / CHCl3; dimethylformamide / 6 h / Heating 5: 31 percent / NH3 / methanol / 144 h / Ambient temperature 6: 65 percent / H2 / 10percent Pd/C / methanol / 2 h / 2585.7 Torr View Scheme

1: 88 percent / 1N NaOH / ethanol; H2O / 4 h / Heating 2: 91 percent / pyridine / 24 h / Ambient temperature 3: 86 percent / LiN3 / dimethylformamide / 2 h / 85 °C 4: 70 percent / 80percent acetic acid / 0.33 h / Heating 5: pyridine / 24 h / 4 °C 6: thionyl chloride / CHCl3; dimethylformamide / 6 h / Heating 7: 31 percent / NH3 / methanol / 144 h / Ambient temperature 8: 65 percent / H2 / 10percent Pd/C / methanol / 2 h / 2585.7 Torr View Scheme

1: 91 percent / pyridine / 24 h / Ambient temperature 2: 86 percent / LiN3 / dimethylformamide / 2 h / 85 °C 3: 70 percent / 80percent acetic acid / 0.33 h / Heating 4: pyridine / 24 h / 4 °C 5: thionyl chloride / CHCl3; dimethylformamide / 6 h / Heating 6: 31 percent / NH3 / methanol / 144 h / Ambient temperature 7: 65 percent / H2 / 10percent Pd/C / methanol / 2 h / 2585.7 Torr View Scheme