Azobisisobutyronitrile → 5-nitro-2,3-dihydro-1H-isoindol-1-one

Participants

Reaction Steps

AIBN (84 mg, 0.51), NBS (1.1 gram, 6.4 mmol), and the methyl 2-methyl-4-nitrobenzoate (1 g, 5.1 mmol) from step 1 of this example were suspended in CCl4 and the mixture heated under N2 at 79 C overnight. The solution was filtered, and concentrated in vacuum. The residue was dissolved in 7 N ammonia in methanol (15 ml) and the solution stirred for 2 hours at RT. The mixture was concentrated in vacuum. and the resulting solid suspended in EtOAc (21.5 ml), heated at 80° C. for 30 minutes with stirring, cooled RT and aged at −20° C. for the 3 days. The solid was isolated by filtration to give the titled compound.

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