Dimethylformamide → 2-Chloro-6-nitroaniline

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1-chloro-3-nitrobenzene (3.1 g, 0.0197 mol) and o-methoxylamine hydrochloride (2.02 g, 0.0236 mol) were dissolved in N,N-dimethylformamide (15 mL). The solution was added drop wise in 15 min to a suspension of cuprous chloride and potassium tert-butoxide (11.07 g, 0.965 mol) in N,N-dimethylformamide (15 mL) cooled in a 15° C. bath. The cold bath was removed; the mixture was allowed to come to RT and stirred for 1 h. The reaction was quenched with aqueous ammonium chloride solution and extracted with ethyl acetate (4×100 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate, concentrated under vacuum and purified by silica gel column chromatography to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ 8.020-7.994 (dd, J=8.8 Hz, 10.4 Hz, 1H), 7.696-7.674 (dd, J=7.2 Hz, 8.8 Hz, 1H), 7.229 (bs, 1H), 6.705-6.664 (t, J=8.4 Hz, 1H).

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