2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → N-benzyl-3-methyl-6-(2-nitrophenyl)phthalimide

Participants

Reaction Steps

30 ml of chlorobenzene was added to a mixture of 5.0 g of N-benzyl-3-methyl-6-(2-nitrophenyl)-1,2,3,6-tetrahydrophthalimide and 7.0 g of DDQ. The mixture was refluxed for 8 hours, then cooled to room temperature. Thereto was added 100 ml of ethyl acetate. The resulting mixture was washed with aqueous 10% potassium carbonate solution and an aqueous saturated sodium chloride solution in this order and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene/ethyl acetate=100/1 to 80/1), followed by recrystallization from ethanol to obtain 2.0 g (yield: 40%) of N-benzyl-3-methyl-6-(2-nitrophenyl)phthalimide as light yellow crystals.

Provenance & Evidence