Acetic Acid → HCID 14502048, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.11 mole of butyl lithium in 68 ml of hexane and 150 ml of tetrahydrofuran was added a solution of 15.80 g of 3-bromopyridine in 20 ml of tetrahydrofuran at -78° C. After stirring for 30 minutes at -78° C., a solution of 24.63 g of N-(2-diethylaminoethyl)phthalimide in 30 ml of tetrahydrofuran was added to the mixture. After stirring at -78° C. for 1 hour, a solution of 6.61 g of acetic acid in 30 ml of tetrahydrofuran was added, and the mixture was concentrated under reduced pressure. To the residue were added 300 ml of water and 300 ml of ethyl ether, and pH of the mixture was adjusted to 1.5 with 4N-hydrochloric acid. After shaking, the organic layer was discarded and 200 ml of methylene chloride was added to the aqueous layer. The pH was adjusted to 10 with 10N-sodium hydroxide solution. After shaking, the aqueous layer was discarded and the organic layer was washed with saturated aqueous sodium chloride solution. After drying over anhydrous sodium sulfate, the organic layer was concentrated under reduced pressure. The crude product obtained was subjected to silica gel column chromatography (ethyl acetate:triethylamine=20:1). A major fraction was concentrated under reduced pressure to give 16.99 g of 2-(2 -diethylaminoethyl)-3-hydroxy-3-(3-pyridyl)isoindolin-1-one (Compound 21).

Provenance & Evidence