Triethylamine → HCID 86616899, compound

Participants

Reaction Steps

Hydroxylamine hydrochloride (5.74 g, 82.6 mmol) and triethylamine (31.4 mL, 225 mmol) were sequentially added to a solution of (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetaldehyde (14.2 g, 75.1 mmol) in dichloromethane. The resultant suspension was stirred at room temperature for several hours and adjusted to pH 6 with the addition of saturated aqueous ammonium chloride. The aqueous layer was then separated and extracted with several portions of dichloromethane. The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on a vacuum filter funnel (silica gel, eluting with 3% to 5% methanol in dichloromethane). The product was then dissolved in dichloromethane, and the solution was washed with 1 N hydrochloric acid. The aqueous layer was extracted a few times with dichloromethane, and the combined organic fractions were dried over magnesium sulfate, filtered, and concentrated to provide 13.05 g of (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethanal oxime as a white solid.

Provenance & Evidence