Réaction #75288

Équation de réaction

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

Solvants

acetic acid

Conditions de réaction

Traitement

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

Mode opératoire

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