Reaction #43994

Reaction equation

1,4-Diethoxy-2,3-naphthalenedicarboxylic anhydride

ethyl (4-aminophenyl)acetate

water

→

ethyl[4-(4,9-diethoxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate

Solvents

acetic acid

Conditions

Workup

1. 1
   FiltrationThe white solid was filtered
2. 2
   Washwashed with water
3. 3
   workup.DISSOLUTIONdissolved in dichloromethane (800 ml)
4. 4
   WashThe solution was washed with water, brine
5. 5
   Dryingdried (MgSO4)
6. 6
   Otherthe solvent evaporated under vacuum

Procedure

1,4-Diethoxy-2,3-naphthalenedicarboxylic anhydride (23.3 g, 81.5 mmol) and ethyl (4-aminophenyl)acetate (14.8 g, 82 mmol) were refluxed under nitrogen in acetic acid (160 ml) overnight. The mixture was cooled to room temperature and poured into water (1 L). The white solid was filtered, washed with water and dissolved in dichloromethane (800 ml). The solution was washed with water, brine and dried (MgSO4) and the solvent evaporated under vacuum to give ethyl[4-(4,9-diethoxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate as an off-white solid, 33 g, 96%.

Source