Hydrochloric Acid → HCID 15892659, compound

Participants

Reaction Steps

A solution of sodium nitrite in water (4.2 g, 60 mmol, 5 M, 12 mL) was added dropwise to a cooled (0° C.) solution of 4-ethyl-3-nitroaniline (10 g, 60 mmol) in HCl (conc., 200 mL) and the reaction mixture was stirred at the same temperature for 1.5 h. Copper(I) chloride (9.5 g, 96 mmol) was then added and the solution was stirred at r.t. for 1 h and then at 80° C. for an additional hour. After cooling down the reaction mixture was extracted with DCM (3×100 mL) and the combined organic layers were dried over sodium sulfate. The crude was then purified by flash chromatography (hexane:AcOEt 9:1) to obtain the title compound as a yellow oil (6.28 g, 56%).

Provenance & Evidence