Hydrochloric Acid → HCID 12109165, compound

Participants

Reaction Steps

A solution of methyl (R)-3-amino-4-(1-acetamidoethyl)benzoate (600 mg) in acetic acid (6 ml) was dropwise added to a solution of sodium nitrite (193 mg) in conc. sulfuric acid (2 ml) at room temperature, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was dropwise added to a solution of copper(I) chloride (550 mg) in conc. hydrochloric acid (6 ml) under ice-cooling, and the mixture was stirred at room temperature for 5 hours. After the reaction, the reaction mixture was poured into ice water, and extracted with chloroform. The extract was washed with water, dried, and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to give 460 mg of methyl (R)-4-(1-acetamidoethyl)-3-chlorobenzoate.

Provenance & Evidence