Sodium Hydroxide → 4-(2-Fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

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Ethyl 4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate (140 mg, 0.34 mmol) was suspended in EtOH (10 mL), to which was added 1 M NaOH (10 mL). This mixture was stirred at R.T. for 15 h., then diluted with 1 M HCl (50 mL) and the resulting precipitate extracted into EtOAc (2×50 mL). The combined EtOAc fractions were dried (Na2SO4) and the solvent removed under reduced pressure to afford 4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid as a white solid (132 mg, 100%), m.p. (acetone/MeOH) 254-257° C. 1H NMR [(CD3)2SO, 400 MHz] δ 13.30 (v br s, 1H), 9.66 (s, 1H), 8.52 (s, 1H), 7.76 (dd, J=10.1, 1.9 Hz, 1H), 7.59 (ddd, J=8.4, 1.7, 0.8 Hz, 1H), 7.31 (t, J=8.5 Hz, 1H), 5.49 (d, J=0.7 Hz, 1H), 3.41 (s, 3H). Anal. Calcd for C13H10FIN2O3: C, 40.2; H, 2.6; N, 7.2. Found: C, 40.5; H, 2.3; N, 7.3.

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