反应详情

温度

0 °C

3-(Benzyloxy)pyridin-2-amine (25.0 g, 124.9 mmol) was added to acetonitrile (300 mL) and cooled to 0° C. 1-Bromopyrrolidine-2,5-dione (22.22 g, 124.9 mmol) was added portionwise and the reaction mixture was stirred for 15 minutes, then concentrated to dryness. The residue was dissolved in EtOAc and partitioned with water. The organic layer was washed twice with saturated sodium bicarbonate and once with brine. Activated charcoal was added to the organic layer, and the organic layer was warmed to reflux, then cooled, filtered through a plug of celite, and concentrated to give 9.4 g of the title compound. The celite and charcoal were resuspended in EtOAc and filtered through a celite plug to give an additional 3.6 g of the title compound, to provide a total of 12.0 g (34.3% yield). 1H NMR (CDCl3) δ 7.74 (d, 1H), 7.41 (m, 5H), 7.08 (d, 1H), 5.04 (s, 2H), 4.74 (bs, 2H). Mass spectrum (apci) m/z=279.1 (M+H).

1. concentrationconcentrated to dryness
2. dissolutionThe residue was dissolved in EtOAc
3. custompartitioned with water
4. washThe organic layer was washed twice with saturated sodium bicarbonate and once with brine
5. additionActivated charcoal was added to the organic layer
6. temperaturethe organic layer was warmed
7. temperatureto reflux
8. temperaturecooled
9. filtrationfiltered through a plug of celite
10. concentrationconcentrated