55150-07-7

85-91-6

55150-07-7

General procedure for the synthesis of methyl 5-chloro-2-(methylamino)benzoate from methyl 2-(methylamino)benzoate: 36.21 g (0.25 mol) of calcium hypochlorite and 150 mL of distilled water were added to a 500 mL three-necked flask, and cooled in an ice-water bath. Subsequently, 36mL of glacial acetic acid was added and ice water bath conditions were maintained until the solution took on a light yellow color. A mixture consisting of 28.13 g (0.17 mol) of methyl o-methylbenzoate and 100 mL of acetone was slowly added dropwise, and the reaction continued to be stirred in an ice water bath for 2 hours. Upon completion of the reaction, the reaction mixture was diluted by adding 100 mL of distilled water and extracted with ether. All ether extracts were combined, the organic layer was washed sequentially with saturated NaHCO3 solution, dried with anhydrous magnesium sulfate, filtered to remove the desiccant, and the filtrate was concentrated under reduced pressure to give 25.43 g of dark brown liquid product. The crude product did not need further purification and could be used directly in the subsequent reaction.