反应详情

N-(2-Benzyloxy-4-nitro-phenyl)-acetamide (418) (5 g, 17.5 mmol) was dissolved in a mixture of EtOAc (25 mL) and EtOH (25 mL). The solution was chilled on an ice bath. Raney Nickel (5 mL, 50% slurry in water) followed immediately by anhydrous hydrazine (10 mL) were added. Violent bubbling was observed. The ice bath was removed after 10 minutes and the slurry continued to stir until all bubbling had ceased (˜30 minutes). LC-MS and TLC (Rf: 0.15 compared to Rf: 0.5 for compound 418 in 1:1 hexane/EtOAc) indicated complete reduction at this point. The reaction mixture was passed through a plug of silica gel, concentrated, dissolved in EtOAc (250 mL), washed with water (2×75 mL), brine (2×75 mL), dried over MgSO4 and concentrated to give the desired product (419) as a beige solid (3.82 g, 14.9 mmol, 85.3% yield). LC-MS (ESI): (exact mass: 256.12) m/e=257.1 [M+1]+ (100%), 513.2 [2M+1]+ (15%).

1. temperatureThe solution was chilled on an ice bath
2. additionwere added
3. customViolent bubbling
4. customThe ice bath was removed after 10 minutes
5. custom(˜30 minutes)
6. concentrationconcentrated
7. dissolutiondissolved in EtOAc (250 mL)
8. washwashed with water (2×75 mL), brine (2×75 mL)
9. dry with materialdried over MgSO4
10. concentrationconcentrated