4-Chloroaniline → HCID 14476376, compound

Participants

Reaction Steps

Para-toluenesulphonic acid (50 mg) is added to an agitated solution of 2-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-3-hydroxy-1-isoindolinone (10 g) and 4-chlorophenylamine (4.6 g) in xylene (230 cc) at a temperature close to 20° C. in a Dean Stark apparatus. Agitation is continued for 6 hours at a temperature close to 135° C. After cooling to a temperature close to 20° C., the precipitate formed is filtered, washed with xylene (2×50 cc), dried under reduced pressure (20 mm Hg; 2.7 kPa) and recrystallized from boiling acetonitrile (360 cc). 7.1 g of 3-(4-chlorophenylamino)-2-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1-isoindolinone are obtained, melting at 188° C.

Provenance & Evidence