Hydrochloric Acid → ethyl 3-[N-(2-chlorobenzyl)acetylamino]-4-nitrobenzoate

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Reaction Steps

A solution of 1.706 g of ethyl 3-acetylamino-4-nitrobenzoate in 12 ml of N,N-dimethylformamide were added 0.406 g of 60% sodium hydride while being cooled with ice, and the mixture was stirred at room temperature for 40 minutes. A solution of 1.806 g of 2-chlorobenzyl bromide in 10 ml of N,N-dimethylformamide was added thereto, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into cold 1-N hydrochloric acid, and the mixed solution was extracted twice with ethyl acetate. The organic layer was washed with 1-N hydrochloric acid and then with water, and was dried. The solvent was distilled off under reduced pressure. The residue was purified through silica-gel column chromatography (eluent: a mixture of ethyl acetate and hexane at a ratio of from 1:10 to 1:4) to give 2.08 g of oily ethyl 3-[N-(2-chlorobenzyl)acetylamino]-4-nitrobenzoate.

Provenance & Evidence