Pyridine → 5,6-Dihydroxy-4-nitro-2-benzofuran-1,3-dione

Participants

Reaction Steps

5-Hydroxy-6-methoxy-4-nitro-isobenzofuran-1,3-dione (115 mg), aluminum chloride (80 mg) was mixed with ethyl acetate (3 ml). Pyridine (155 μl) in ethyl acetate (2 ml) was added dropwise. The resulting mixture was stirred at room temperature for 0.5 hours, heated to reflux for 3 hours, and then quenched with water (0.5 ml) and conc. HCl (0.5 ml) at 60° C. Ethyl acetate and water was removed in vacuo. The remainder was mixed with brine (2 ml) and extracted two times with ethyl acetate (15 ml). The combined organic layers were dried over anhydrous Na2SO4, filtrated, evaporated and triturated with diethyl ether.

Provenance & Evidence