Methyl iodide → 2-(Methylamino)-4-nitrophenol

Triethylamine (2 ml, 14.4 mmol) was added to a solution of 2-amino-4-nitrophenol (1) (1.54 g, 10 mmol) and methyl iodide (1 ml, 16 mmol) in methanol (10 ml). After 1 hour at 40° C., further methyl iodide (1 ml) and triethylamine (1 ml) were added and the mixture was stirred at 40° C. for a further 2 hours. The reaction mixture was concentrated to dryness in vacuo, the residue was added to aqueous 2N sodium acetate solution and the mixture was extracted with ethyl acetate. The organic phase was dried with sodium sulfate and chromatographed on silica gel (eluent dichloromethane/methanol 95/5). Yield 880 mg (52%).