Hydrochloric Acid → 2-Chloro-1-methoxy-3-nitrobenzene

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Reaction Steps

To a mixture consisting of 15.5 g (92.26 mmol) 2-methoxy-6-nitro-phenylamine, 31 ml water and 31 ml conc. HCl, a solution of 6.36 g (92.26 mmol) NaNO2 in 38 ml water is slowly added dropwise at −10° C.-0° C. After stirring for 0.5 h the mixture is slowly added to a solution of 11.88 g (120 mmol) CuCl in 93 ml conc. HCl. After completion of the addition stirring is continued for 1.5 h at room temperature and for 0.5 h at reflux temperature. The reaction mixture is allowed to cool to room temperature and is poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1) to afford 12.69 of the title compound as a crystalline solid.

Provenance & Evidence