2,4-Difluoroaniline → 2-(2,4-Difluorophenyl)hexahydro-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

8.38 Parts of 2,4-difluoroaniline were added to a solution of 10 parts of cyclohexane-1,2-dicarboxylic anhydride in 100 parts of glacial acetic acid. The mixture was stirred for two hours. The mixture was refluxed for 20 hours and the resulting product was poured into 200 parts of ice. The resulting crystals were filtered and recrystallized twice from 70 parts of methanol at -40° C to yield 10.2 parts of white crystals of 2-(2,4-difluorophenyl)-3a,4,5,6,7,7a-hexahydro-1H-isoindole-1,3(2H)-dione melting at 117°-123° C.

Provenance & Evidence