Benzene, 4-chloro-1-methyl-2-nitro- → 5-Chloro-2-methylaniline

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A 2 L flask was charged the solution of 4-chloro-1-methyl-2-nitrobenzene (60 g, 0.35 mol) in MeOH (1 L), Raney Ni was added, the air in flask was replaced three times with H2, the mixture was stirred for 3 hr at rt. The solution was filtered and concentrated. The residue was dissolved in CH2Cl2 (500 mL), and the solution was washed with brine, dried over Na2SO4. Solvent removal gave 5-chloro-2-methylbenzenamine (50 g, 0.35 mol). 1H NMR (CDCl3, 400 MHz) δ 7.02-6.93 (d, 2H), 6.70-6.60 (d, 2H), 3.67 (s, 2H), 2.14 (s, 3H).

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