3,4,5,6-Tetrahydrophthalic anhydride → N-(2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide

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Reaction Steps

A mixture of 3,4,5,6-tetrahydrophthalic anhydride (22.8 g, 150 mmol), 2-fluoro-5-nitroaniline (23.4 g, 150 mmol) in glacial acetic acid is heated at reflux for 23 hours, cooled and poured into a water/toluene mixture. The organic phase is separated, washed sequentially with water and saturated sodium hydrogen carbonate solution, dried and concentrated in vacuo to obtain a yellow solid. Recrystallization of the solid from ethanol gives the title compound as off-white plates (26.6 g, mp 154°-156° C.) which are identified by 1H and 13C NMR spectral analyses.

Provenance & Evidence