Ammonium Chloride → HCID 23156849, compound

Participants

Reaction Conditions

Reaction Steps

A 1.8 M lithium diisopropylamide THF solution (5.39 ml, 9.69 mmol) was diluted with THF (10 ml). To the diluted solution, a solution obtained by dissolving the 5-chloro-2,N,N-trimethylbenzamide (383 mg, 1.94 mmol) prepared in step A in THF (5 ml) was added dropwise at −78° C. A solution obtained by dissolving 2-(4-morpholino)benzonitrile (438 mg, 2.33 mmol) in THF (5 ml) was further added to the mixture. The obtained mixture was stirred at −78° C. for 30 minutes. Thereafter, a saturated ammonium chloride aqueous solution was added to the reaction solution, followed by extraction with ethyl acetate. The extract was washed with a saturated saline solution, and was then dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The obtained yellow oil product was crystallized from hexane/ethyl acetate (3:1), so as to obtain 7-chloro-3-(2-morpholin-4-ylphenyl)-2H-isoquinolin-1-one (575 mg; yield: 87%) in the form of a colorless crystal.

Provenance & Evidence