2,6-Dinitrotoluene → 3-Methyl-2,4-dinitroaniline

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Reaction Steps

A mixture of 2,6-dinitrotoluene (28 g, 0.15 mol) and hydroxylamine hydrochloride (28 g, 0.15 mol) was stirred in ethanol (700 mL) until completely dissolved. 2N potassium hydroxide solution in methanol (275 mL) was added all at once and the resulting mixture allowed to stir overnight at room temperature. After this time a solution of ammonium chloride (36 g) in water (175 mL) was added and the mixture stirred for an additional hour. The reaction mixture was evaporated under reduced pressure and the residue partitioned between ethyl acetate (300 mL) and saturated brine (250 mL). The ethyl acetate layer was separated, dried over magnesium sulfate and concentrated under reduced pressure. Flash chromatography of the residue (ethyl acetate/hexane (2:1)) afforded the desired product. 1H NMR (400 MHz) (CDCl3) δ 7.98 (d, J=9.4 Hz, 1H); 6.73 (d, J=9.4 Hz, 1H); 5.50 (bs, 2H); 2.59 (s, 3H).

Provenance & Evidence