Sodium Hydroxide → 5-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylic acid

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An aqueous solution of sodium hydroxide (1N, 1.5 mL, 1.5 mmol) was added to a solution of Methyl 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylate (0.275 g, 0.75 mmol) in tetrahydrofuran (5 mL), and the resulting mixture was stirred at ambient temperature for 4 hours. After this time the mixture was diluted with water (4.5 mL) and washed the ethyl ether (2×5 mL). The aqueous phase was then acidified to pH 5 by the addition of hydrochloric acid solution (1 M), then the product was extracted into ethyl acetate (5×5 mL), dried (Na2SO4) and the solvent removed under reduced pressure to afford the title product as a white solid (123 mg, 47% yield). 1H NMR (300 MHz, d6-DMSO) δ: 9.0 (2H, s), 8.1 (1H, s). MS m/z: 350.85, 352.90 [M+H]+.

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