Hydrochloric Acid → 2-(1H-Pyrrol-1-yl)isoindoline-1,3-dione

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Reaction Steps

A solution of N-aminophthalimide (29.0 g, 178.8 mmol) and 2,5-dimethoxytetrahydrofuran (24.2 mL, 187.8 mmol) in anhydrous dioxane (290 mL) was stirred under reflux. While heating so that the resulting solution remained yellow, 5 N hydrochloric acid solution was cautiously added. The resulting mixture was allowed to cool to room temperature. The produced solid was filtered and washed with a 1:3 solution of dioxane and water. The target compound was yielded as a white solid (34.9 g, 164.5 mmol, 92% yield).

Provenance & Evidence