Pyridine → N-methyl-4-(4-(2,2,2-trichloroacetamido)phenoxy)picolinamide

Participants

Reaction Steps

The clear solution of 4-(4-aminophenoxy)-N-methylpicolinamide (100 g, 0.411 mol) in dichloromethane (100 ml) was cooled to 0° C. to −5° C. and pyridine (83 ml, 1.02 mol) was added in one lot to the reaction mass. It was then agitated at same temperature for 15 minutes and a solution of trichloroacetyl chloride (60 ml, 0.535 mol) in dichloromethane (500 ml) was added dropwise maintaining temperature of the reaction mass below 0° C. The reaction mass was then stirred for 2-3 hours below 0° C. and quenched with water (500 ml) below 5° C. The organic phase was then separated and aqueous layer was reextracted with dichloromethane. The combined dichloromethane layer was washed with water, dried over sodium sulfate and evaporated under vacuum to obtain (72 g) of the desired product.

Provenance & Evidence