N([O-])=O.[Na+].O.[N+:6]([C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=1[CH:16]([CH3:18])[CH3:17])N)([O-:8])=[O:7].[ClH:19]>[Cu]Cl>[Cl:19][C:11]1[CH:13]=[CH:14][C:15]([CH:16]([CH3:18])[CH3:17])=[C:9]([N+:6]([O-:8])=[O:7])[CH:10]=1A solution of sodium nitrite in water (3.6 g, 52.2 mmol, 5 M, 10.4 mL) was added drop wise to a solution of 3-nitro-4-(propan-2-yl)aniline (9.4 g, 52.2 mmol) in conc. HCl (175 mL) at 0° C. and the reaction mixture was stirred at the same temperature for 1.5 h. Copper (I) chloride (8.3 g, 83.5 mmol) was then added and the solution was stirred at room temperature 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/EtOAc 95/5) to obtain the title compound as yellow oil (1.8 g, 17%).
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