Reaction #75288

Reaction equation

cis-1,2-cyclohexane dicarboxylic anhydride

4-amino-3-fluorobenzonitrile

→

4-(1,3-dioxo-2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-3-fluorobenzonitrile

Solvents

acetic acid

Conditions

Workup

1. 1
   TemperatureThe mixture was refluxed for 4 hours
2. 2
   workup.ADDITIONpoured over 200 parts of ice
3. 3
   Filtrationfiltered
4. 4
   OtherThe crude crystalline product was recrystallized from methanol

Procedure

To a solution of 5 parts of cis-1,2-cyclohexane dicarboxylic anhydride in 75 parts of glacial acetic acid was added 4.8 parts of 4-amino-3-fluorobenzonitrile in one portion. The mixture was refluxed for 4 hours, poured over 200 parts of ice and filtered. The crude crystalline product was recrystallized from methanol to yield 4.4 parts of beige 4-(1,3-dioxo-2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-3-fluorobenzonitrile melting 120°-123°.

Source