Sodium Hydroxide → 4,5-Dichloro-2-methylaniline

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4,5-Dichloro-2-methyl-nitrobenzene 5 (5.0 g, 24.3 mmol) was heated at 100° C. in titanium trichloride (30% in aqueous hdyrochloric acid, 25 mL) for 2 hrs., cooled to RT, the reaction solution was basified to pH 8 with 50% aqueous sodium hydroxide, then extracted with ethyl acetate. The ethyl acetate layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography using 10% ethyl acetate in hexanes to give 2.4 g (56%) of the title product. 1H NMR (400 MHz, CDCl3) δ7.09 (s, 1 H, Ar), 6.74 (s , 1 H, Ar), 3.63 (s, 2 H, NH2), 2.10 (s, 3H, CH3).

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