Citric Acid → 5-Chloro-2-[(4-chlorophenoxy)methyl]-3-pyridinecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chlorofuro[3,4-b]pyridin-5(7H)-one (step 1, 110 mg, 0.65 mmol) and 4-chloro phenol (416 mg, 3.24 mmol) was heated to 130° C. under N2, then sodium methoxide (28% methanol solution, 250 mg, 1.30 mmol) was added dropwise to the mixture at 130° C. The mixture was heated at the same temperature for 4 hours. After cooling, to the mixture was added 10% aqueous citric acid and the mixture was extracted with ethyl acetate. The extracts were dried over sodium sulfate and evaporated. The residue was purified by flash column chromatography on silica gel to afford 113 mg of the title compound:

Provenance & Evidence