Nitric Acid → 4-Iodo-5-nitro-2,3-dihydrofuro[2,3-b]pyridine

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Reaction Steps

4-Iodo-2,3-dihydrofuro[2,3-b]pyridine (2.237 g, 9.055 mmol) in sulfuric acid (10.0 mL, 188 mmol) at −10° C. was added slowly to a stirred solution of a solution of fuming nitric acid (15.0 mL, 358 mmol) in sulfuric acid (15.0 mL, 281 mmol) slowly over a period of 15 min. The reaction mixture was allowed to warm to room temperature and stirred for 16 h. The reaction mixture was then quenched by addition onto crushed ice and the resulting mixture was extracted with EtOAc (6×100 mL). The combined organic extract was washed with saturated aq. NaHCO3 (2×300 mL) and brine (300 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (0-100% EtOAc in hexanes) to give the sub-title compound as a pale yellow solid (2.43 g, 92%). LCMS calc. for C7H6IN2O3(M+H)+: m/z=292.9. found 293.0.

Provenance & Evidence