Hydrazine → HCID 14166615, compound

Participants

Reaction Steps

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%).

Provenance & Evidence