Triethylamine → 1H-Isoindole-1,3(2H)-dione, 2-(6-chloro-4,5-dimethyl-2-pyridinyl)-

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Reaction Steps

To a solution of 2-(1,3-dioxoisoindolin-2-yl)-4,5-dimethylpyridine 1-oxide (1.5 g, 0.01 mol) in POCl3 (50 mL) was added Et3N (680 mg, 0.01 mol) at room temperature. The mixture was stirred at 80□ for 2 hr, and then carefully poured into the mixture of saturation NaHCO3 solution and ice water. The mixture was extracted with EtOAc (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated under vacuum to give a crude residue that was purified by column chromatography on silica gel (10-15% ethyl acetate in petroleum ether) to give 2-(6-chloro-4,5-dimethylpyridin-2-yl)isoindoline-1,3-dione (650 mg, 41%). 1H NMR (300 MHz, CDCl3) δ 7.97-7.92 (m, 2H), 7.82-7.78 (m, 2H), 7.16 (s, 1H), 2.41 (s, 3H), 2.39 (s, 3H).

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