Methyl iodide → 6-Nitro-o-anisidine

Participants

Reaction Steps

2-Amino-3-nitrophenol (0.5 g, 3.2 mmol) was dissolved in 10 mL 2-butanone, and potassium carbonate (0.54 g, 3.9 mmol) and methyl iodide (0.4 mL) were added. The suspension was stirred overnight at room temperature. The reaction mixture was filtered through a plug of Celite, and the solid residue was washed with ethyl acetate. The resulting filtrate was washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 0.52 g of 2-methoxy-6-nitroaniline, which was used without further purification. 1H-NMR (400 MHz, CDCl3): δ 7.74 (d, 1H), 6.87 (d, 1H), 6.61 (dd, 1H), 6.42 (b, 2H), 3.92 (s, 3H). MS (EI): 169 (MH+).

Provenance & Evidence