3-Amino-N,N-dimethyl-4-nitroaniline → N4,N4-dimethylbenzene-1,2,4-triamine

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A solution of 5-dimethylamino-2-nitroaniline (1.94 g, 10.7 mmol) in 4:1 ethyl acetate/methanol (200 ml) was treated with 5% palladium on carbon (1.12 g) and stirred under an atmosphere of hydrogen at room temperature for 20.5 h. The suspension was quickly filtered through celite, the residue washed with methanol and the combined filtrate and washings concentrated to give the crude 2-amino-4-(dimethylamino)aniline as a dark brown oil, which was used without further purification in the next step.

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