3-Aminophenol → 4,5,6,7-Tetrahydro-2-(3-hydroxyphenyl)-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

A mixture of 25.0 g of 3,4,5,6-tetrahydrophthalic anhydride (THPA), 17.9 g of 3-aminophenol and 350 mL of glacial acetic acid was refluxed for 1 hour, then cooled and poured slowly into 1400 mL of ice-water. The resulting mixture was filtered, the collected solids were washed with cold water and dried (oven, reduced pressure) to give N-(3-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide (1A), as yellow crystals, m.p.: 196°-197.5° C.

Provenance & Evidence