反应详情

To a mixture of (2-cyano-5-nitrobenzyl)carbamic acid t-butyl ester (2.39 g) and ethanol (180 mL) there were added water (12 mL), saturated aqueous ammonium chloride (5 mL) and iron powder (2.02 g), under a nitrogen atmosphere. The mixture was heated to reflux for 2 hours and then filtered through Celite to obtain a filtrate, and the solvent in the filtrate was distilled off under reduced pressure to obtain a residue. The Celite and filtered substance were washed with ethyl acetate (400 mL) and water (200 mL) in that order, and this washed solution was combined with the previous residue. After sufficiently shaking the mixture, the organic layer was separated off and the organic layer was dried over anhydrous magnesium sulfate. The mixture was filtered to obtain a filtrate, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture) to obtain the target compound (1.97 g) as an off-white solid.

1. temperatureThe mixture was heated
2. temperatureto reflux for 2 hours
3. filtrationfiltered through Celite
4. customto obtain a filtrate
5. distillationthe solvent in the filtrate was distilled off under reduced pressure
6. customto obtain a residue
7. filtrationThe Celite and filtered substance
8. washwere washed with ethyl acetate (400 mL) and water (200 mL) in that order
9. customthe organic layer was separated off
10. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
11. filtrationThe mixture was filtered
12. customto obtain a filtrate
13. distillationthe solvent in the filtrate was distilled off under reduced pressure
14. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture)