反应详情

Acetic acid (3 ml) was added to (E)-N-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-N-methyl-3-(3-pyridyl)-2-propenoic acid amide (165 mg, 0.5 mmol) and allowed to stand at −20° C. After acetic acid was solidified, 50% aqueous hydroxylamine solution (0.62 ml, 10 mmol) was added under ice-cooling and reacted at the same temperature. After warming to room temperature and reacting for further 22 hours, water (10 ml) and ethyl acetate (10 ml) were added and extracted three times with ethyl acetate (10 ml). The organic layer was washed sequentially with water (40 ml) and aqueous saturated sodium chloride solution (40 ml) and dried over anhydrous magnesium sulfate (10 g). The drying agent was removed out and the filtrate was concentrated. The resulting dry product was purified by a column chromatography using silica gel (20 g) (elution with dichloromethane: methanol=100:3.5). After purification, the product was recrystallized in ethyl acetate (5 ml) and n-hexane (15 ml) to yield the titled compound (91 mg, yield 51%).

1. customto stand at −20° C
2. temperaturecooling
3. customreacted at the same temperature
4. extractionextracted three times with ethyl acetate (10 ml)
5. washThe organic layer was washed sequentially with water (40 ml) and aqueous saturated sodium chloride solution (40 ml)
6. dry with materialdried over anhydrous magnesium sulfate (10 g)
7. customThe drying agent was removed out
8. concentrationthe filtrate was concentrated
9. customThe resulting dry product was purified by a column chromatography
10. customAfter purification
11. customthe product was recrystallized in ethyl acetate (5 ml)