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

Participants

Reaction Steps

Chloroacetone (84.5 mL) was added dropwise to a DMF (497 mL) mixture of methyl 4-formylamino-3-methoxybenzoate (111 g), cesium carbonate (346 g), and potassium iodide (8.78 g) at room temperature, and the reaction liquid was stirred for 3 hours. Cesium carbonate (173 g) and chloroacetone (42.0 mL) were further added to the reaction liquid, which was then stirred at room temperature for 2 hours. Ice water and ethyl acetate were added to the reaction liquid to separate an organic layer. Ethyl acetate was added to the aqueous layer to separate an organic layer. The organic layers were combined, which was then washed with water and saturated saline in that order, followed by drying the resultant organic layer with anhydrous magnesium sulfate before concentrating the organic layer under reduced pressure. The residue was diluted with toluene, followed by concentrating the solution under reduced pressure. To the resultant residue were added tertiary-butyl methyl ether and heptane, and the precipitated solid was collected by filtration and washed with a heptane solution of 50% tertiary-butyl methyl ether. The resultant solid was air-dried overnight to provide 118 g of the title compound.

Provenance & Evidence