Acetic Acid → HCID 57879556, compound

Participants

Reaction Steps

0.31 g of iron powder was added to a mixed solution of 5.3 mL of methanol and 1.6 mL of acetic acid containing 0.53 g of methyl 2-nitro-4-(phenoxymethyl)benzoate, and the resulting mixture was heated to reflux for 3 hours. The reaction mixture was cooled to room temperature and ethyl acetate and a saturated sodium hydrogen carbonate aqueous solution were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in 5.3 mL of methylene chloride and 0.51 mL of triethylamine and 0.26 mL of benzoyl chloride were added while ice-cooled sequentially and stirred at room temperature for 15 hours. The solvent was evaporated under reduced pressure and ethyl acetate and 1.0 mol/L hydrochloric acid were added to the obtained residue. The organic layer was separated and washed with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue and a solid substance was separated by filtration to obtain 0.31 g of methyl 2-(benzamido)-4-(phenoxymethyl)benzoate as white solid.

Provenance & Evidence