反应详情

2-(4-(4-methoxyphenylamino)-3-nitrophenyl)benzoxazole (Working Example 15-3) (150 mg, 0.415 mmol) was added to a tetrahydrofuran (5 mL) solution containing 10% palladium-carbon (50 mg), and a hydrogen atmosphere was substituted in the flask and this was stirred at room temperature for 3 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. To a solution of the oil obtained in toluene (5 mL) was added acetyl chloride (70.8 mg, 0.902 mmol), and this was heated to reflux with stirring for 2.5 hours. After the reaction was complete, this was cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was added, and this was extracted with ethyl acetate. The organic layer obtained was dried over anhydrous sodium sulfate, filtered, and concentrated to give crystals that were purified by silica gel column chromatography to yield the title compound (47 mg, 32% yield) as dark brown crystals.

1. filtrationthis was filtered through Celite
2. concentrationthe filtrate was concentrated
3. customTo a solution of the oil obtained in toluene (5 mL)
4. temperaturethis was heated
5. temperatureto reflux
6. stirringwith stirring for 2.5 hours
7. temperaturethis was cooled to room temperature
8. extractionthis was extracted with ethyl acetate
9. customThe organic layer obtained
10. dry with materialwas dried over anhydrous sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customto give crystals that
14. customwere purified by silica gel column chromatography