Acetic Acid → 2-[[4-(Methylthio)phenyl]amino]isonicotinic acid

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To a solution of 2-fluoroisonicotinic acid (620 mg, 4.95 mmol) and 4-(methylthio)aniline (0.984 mL, 8.42 mmol) in N,N-dimethylformamide (20 mL) was added sodium hydride (792 mg, 19.8 mmol), and the resulting mixture was stirred under an argon atmosphere at 85° C. for 5 hr. After cooling, acetic acid (1.2 mL) was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Ethyl acetate and water were added to the residue, the mixture was stirred for 20 min, and the precipitate was collected by filtration to give crude 2-[[4-(methylthio)phenyl]amino]isonicotinic acid.

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