Ethanol → 5-[(4-Fluorophenyl)methyl]-3-{[4-(methyloxy)phenyl]amino}-2-pyridinecarboxylic acid

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Reaction Conditions

Reaction Steps

5-[(4-fluorophenyl)methyl]-3-{[4-(methyloxy)phenyl]amino}-2-pyridinecarbonitrile (505 mg, 1.52 mmol) was dissolved in ethanol (50 mL) and 50% sodium hydroxide was added and the mixture was heated at 100° C. for 1 hour. The reaction was cooled to ambient temperature, concentrated under reduced pressure, and acidified with 6 N hydrochloric acid. The aqueous layer was extracted with ethyl acetate and the organics were dried over sodium sulfate and concentrated under reduced pressure to yield 5-[(4-fluorophenyl)methyl]-3-{[4-(methyloxy)phenyl]amino}-2-pyridinecarboxylic acid (560 mg, 95% yield). 1H NMR (CDCl3/methanol-d4) δ 7.95 (s, 1 H), 7.32 (s, 1 H), 7.01-6.98 (m, 4 H), 6.93-6.83 (m, 4 H), 3.86 (s, 2 H), 3.75 (s, 3 H); MS m/z 353 (M+1).

Provenance & Evidence