Chloroacetone → Methyl 4-[formyl-(2-oxopropyl)amino]-3-methoxybenzoate

Participants

Reaction Steps

To a mixture of methyl 4-(formylamino)-3-methoxybenzoate (25.8 g), cesium carbonate (80.4 g) and potassium iodide (2.04 g) in DMF (115 mL) was added dropwise chloroacetone (19.6 mL) at room temperature, and the mixture was stirred at room temperature for 3 hr. Cesium carbonate (40.2 g) and chloroacetone (9.8 mL) were added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr. Ice water and ethyl acetate were added to the reaction mixture, and the organic layer was separated. To the aqueous layer was added ethyl acetate, and the organic layer was separated. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (32.6 g).

Provenance & Evidence