Aniline → Methyl 4-(anilino)-2-(benzamido)benzoate

Participants

Reaction Steps

0.16 mL of aniline, 0.12 g of 1,1′-bis(diphenylphosphino)ferrocene, 0.057 g of (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride methylene chloride complex and 0.17 g of sodium tert-butoxide were added to 6 mL of dioxane solution containing 0.58 g of methyl 2-(benzamido)-4-bromobenzoate, and the resulting mixture was heated to reflux under nitrogen atmosphere for 4 hours. After the reaction mixture was cooled to room temperature, 1 mL of acetic acid was added and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to obtain 0.43 g of methyl 4-(anilino)-2-(benzamido)benzoate as colorless oil.

Provenance & Evidence