4-Nitrobenzoic Acid → Ethyl 3-[(4-nitrobenzoyl)amino]propanoate

Participants

Reaction Steps

To a mixture of 4-nitrobenzoic acid (16.7 g), β-alanine ethyl ester hydrochloride (18.4 g), 1-hydroxybenzotriazol.monohydrate (18.4 g), triethylamine (16.7 mL) and N,N-dimethylformamide (200 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (23.0 g), and the mixture was stirred at room temperature for 8 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate, dried over magnesium sulfate, and concentrated under reduced pressure to give a white solid. Recrystallization from ethyl acetate-hexane gave the title object compound (26.6 g, 100%) as white crystals.

Provenance & Evidence