反应详情

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.

1. customThe aqueous layer was then separated
2. extractionextracted with several portions of dichloromethane
3. dry with materialThe combined organic fractions were dried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by chromatography on a vacuum
7. filtrationfilter funnel
8. wash(silica gel, eluting with 3% to 5% methanol in dichloromethane)
9. dissolutionThe product was then dissolved in dichloromethane
10. washthe solution was washed with 1 N hydrochloric acid
11. extractionThe aqueous layer was extracted a few times with dichloromethane
12. dry with materialthe combined organic fractions were dried over magnesium sulfate
13. filtrationfiltered
14. concentrationconcentrated