Sodium Hydroxide → 5-(4-Fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acid

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Reaction Steps

A mixture of ethyl 5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylate (1.1 g, 4 mmol) and NaOH (1.6 g, 40 mmol) in water (25 mL) was stirred at RT overnight. The mixture was washed with EtOAc (2×) and the aqueous layer was acidified to pH=1-2 with conc. HCl. The resulting precipitate was collected by filtration and dried under vacuum to afford 5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acid (810 mg, 81.9% yield). 1H-NMR (400 MHz, CDCl3): δ 15.76 (s, 1H), 8.49 (d, J=2.4 Hz, 1H), 7.58 (m, 3H), 7.14 (t, J=8.8 Hz, 2H), 3.92 (s, 3H).

Provenance & Evidence