2-Chloro-3-nitro-6-methylpyridine

39745-39-6

56057-19-3

2-Hydroxy-3-nitro-6-methylpyridine (compound 25, 10 g, 0.065 mol) was added to 50 mL of phosphoryl chloride and heated to reflux for 4 hours. Upon completion of the reaction, most of the phosphorus trichloride was removed by distillation under reduced pressure. The residue was slowly poured into 200 g of ice water and stirred for 2 hours. A large amount of precipitate appeared in the reaction mixture and the precipitate was collected by filtration under reduced pressure and dried under vacuum to give 10 g of white solid product (compound 26) in 89% yield. The melting point of the product was 68.5-70.5 °C (water) [J.O.C., 1955, 20, 1729-1731].