2,4,6-Trifluoroaniline → 2-(2,4,6-Trifluorophenyl)hexahydro-1H-isoindole-1,3(2H)-dione
Reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[C:3]=1[NH2:4].[CH:11]12[C:20](=O)[O:19][C:17](=[O:18])[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]2>C(O)(=O)C>[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[C:3]=1[N:4]1[C:17](=[O:18])[CH:12]2[CH:11]([CH2:16][CH2:15][CH2:14][CH2:13]2)[C:20]1=[O:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
9.54 Parts of 2,4,6-trifluoroaniline were added to a solution of 10 parts of cyclohexane-1,2-dicarboxylic anhydride in 100 parts of glacial acetic acid. The mixture was refluxed for 20 hours and the resulting mixture was poured into 200 parts of ice. The resulting crystals were filtered, dried and recrystallized twice from 70 parts of methanol at -40° C to yield 8.3 parts of white crystals of 2-(2,4,6-trifluorophenyl)-3a,4,5,6,7,7a-hexahydro-1H-isoindole-1,3(2H)-dione melting at 129°-131° C.