反应详情

温度

-10 °C

Concentrated nitric acid (10 mL, >69% pure) was added to acetic anhydride (100 mL) cooled to −10° C. The solution was treated portionwise with N-[4-(cyanomethyl)phenyl]acetamide (5.0 g, 28.7 mmol) at a rate which maintained an internal temperature below −5° C. The solution was stirred for 1 hour while warming to room temperature. The solution was poured into an ice/water mixture and extracted several times with ethyl acetate. The combined extracts were washed with 10% Na2CO3 and brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate to provide 4.82 g (77%) of N-[4-(cyanomethyl)-2-nitrophenyl]acetamide.

1. temperaturemaintained an internal temperature below −5° C
2. temperaturewhile warming to room temperature
3. extractionextracted several times with ethyl acetate
4. washThe combined extracts were washed with 10% Na2CO3 and brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. customThe residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate