反应详情

温度

70 °C

To a solution of 2-chloro-5-nitropyridine (15.0 g, 94.5 mmol) and tert-butyl (3-hydroxy-4-methylphenyl)carbamate (20.0 g, 90.0 mmol) in N,N-dimethylformamide (200 mL) was added potassium carbonate (18.6 g, 135 mmol), and the mixture was stirred at 70° C. for 18 hr. The reaction mixture was cooled to room temperature, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Water (400 mL) was added to the obtained residue, and the mixture was extracted with ethyl acetate (400 mL×2). The combined organic layer was washed with saturated brine (300 mL×2), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate), and the obtained solution was concentrated under reduced pressure. The residue was triturated with hexane to give the title compound (28.6 g, 92%) as a pale-yellow solid.

1. temperatureThe reaction mixture was cooled to room temperature
2. filtrationthe insoluble material was filtered off
3. concentrationthe filtrate was concentrated under reduced pressure
4. additionWater (400 mL) was added to the obtained residue
5. extractionthe mixture was extracted with ethyl acetate (400 mL×2)
6. washThe combined organic layer was washed with saturated brine (300 mL×2)
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationThe insoluble material was filtered off
9. concentrationthe filtrate was concentrated under reduced pressure
10. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate)
11. concentrationthe obtained solution was concentrated under reduced pressure
12. customThe residue was triturated with hexane