4-Nitroaniline → Methyl 2-[(4-nitrophenyl)amino]-3-oxobutanoate

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, to a solution of 4-nitroaniline (3.84 g) in toluene (278 mL) were added methyl 2-diazo-3-oxobutanoate (5.13 g) and rhodium(II) acetate dimer (250 mg), and the mixture was stirred at 120° C. for 1 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=9:1→hexane:ethyl acetate=7:3 (volume ratio)] to give the title compound (4.63 g, yield 98%) as a yellow solid.

Provenance & Evidence