Phthalic Anhydride → 2-(2-Chloropyridin-3-yl)-1H-isoindole-1,3(2H)-dione

Participants

Reaction Conditions

Reaction Steps

A stirred slurry containing 15 grams of phthalic anhydride, 13 grams of 3-amino-2-chloropyridine, one gram of toluenesulfonic acid and 200 ml. of o-dichlorobenzene was heated at reflux for 6 hours. During this heating period 100 ml. of solvent and 1.8 ml. of water were removed. After cooling to 30° C., 50 ml. of heptane and 10 ml. of water were added and stirring was continued. The solid was collected by filtration and air dried. A 99 percent yield of N-(2-chloro-3-pyridyl) phthalimide, m.p. 156°-7° C., was obtained.

Provenance & Evidence