Methyl 4-aminobenzoate → HCID 821139, compound

Participants

Reaction Steps

Formic acid (90.0 mL) was added to a dichloromethane solution (900 mL) of methyl 4-aminobenzoate (90.0 g) and to the mixture was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (114 g) at 5° C. over thirty minutes, and then the mixture was stirred at room temperature for three hours. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution (1.2 L) and the pH was adjusted to 10 with 1N sodium hydroxide, and the residue was separated. The aqueous layer was extracted with dichloromethane, and the organic layer was combined and washed with 1N hydrochloric acid, water and brine successively. After the organic layer was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the residue obtained was washed with ethyl acetate to obtain the titled compound (88.7 g) as crystals.

Provenance & Evidence