Nitric Acid → 4-Fluoro-2-methyl-5-nitroaniline

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Concentrated nitric acid (17 g, 0.18 mol) was added dropwise to a stirred solution of 4-fluoro-2-methylaniline (20 g, 0.16 mol) in cone H2SO4 (300 mL) at −10° C. The mixture was stirred at −10° C. for 10 min., and the reaction mixture was poured into ice water. The resultant solid was collected by filtration and partitioned between EtOAc and aq Na2CO3 solution (pH 8). The organic solution was washed with brine, dried (MgSO4) and concentrated to give 4-fluoro-2-methyl-5-nitroaniline (20 g, 74% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.27 (d, J=6.8 Hz, 1 H), 7.14 (d, J=12.4 Hz, 1 H) 5.37 (s, 2 H), 2.10 (s, 3 H).

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