Abstract Two 2, 3-dihydro-2-(4-pyridinyl)-1H-isoindoles 2a, b have been synthesized by the reaction of isoindoline with 4-chloropyridines. In addition, a number of 1-alkyl-2, 3-dihydro-2- (4-pyridinyl)-1H-isoindoles 2c-h were obtained from 2-(4-pyridinyl) phthalimide (5). The addition of alkyl Grignard reagents to 5 gave 1-alkylhydroxyisoindolones 6a-f which, in two cases 6a, b, were dehydrated and subjected to three separate reductions to give targets ...