thionyl chloride in 1,4-dioxane; pyridine 1 h; Heating;

1: 33 percent / NaOH / dioxane 2: 72 percent / SOCl2 / pyridine View Scheme

1: NH3 / methanol / 4 h / Ambient temperature 2: 70 percent / NaOH / dimethylformamide / 1.5 h / Heating 3: 89 percent / SOCl2 / pyridine; dioxane / 1 h / Heating View Scheme

1: 66 percent / Dowex 50 (H+) / methanol / 2 h / Ambient temperature 2: NH3 / methanol / 4 h / Ambient temperature 3: 70 percent / NaOH / dimethylformamide / 1.5 h / Heating 4: 89 percent / SOCl2 / pyridine; dioxane / 1 h / Heating View Scheme