Pyridine → 5,6-Dihydroxy-4,7-dinitro-2-benzofuran-1(3H)-one

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Reaction Steps

5-Hydroxy-6-methoxy-4,7-dinitro-3H-isobenzofuran-1-one (210 mg) was dissolved in ethyl acetate (2.5 ml) followed by addition of aluminum chloride (132 mg) in nitrogen atmosphere. Pyridine (265 μl, 3.28 mmol) was added dropwise. The resulting mixture was heated to reflux for 2 hours, and then quenched with water (0.5 ml) and conc. HCl (0.5 ml) at 75° C. Ethyl acetate (15 ml) was added and phases were separated. The aqueous layer was extracted once with ethyl acetate (15 ml). The combined organic layers were dried over anhydrous Na2SO4. The product was filtrated, evaporated to dryness and recrystallized from heptane-toluene-ethyl acetate.

Provenance & Evidence