Methyl iodide → 6-Nitro-o-anisidine

Participants

Reaction Steps

Tetrabutylammonium iodide (0.4 g), sodium hydroxide (4.0 g) in water (40 ml) and iodomethane (3.4 ml) were added to 2-amino-3-nitrophenol (4.0 g) dissolved in tetrahydrofuran (80 ml) at ambient temperature. This mixture was stirred overnight then concentrated in vacuo. After pouring into water (200 ml) it was extracted into ethyl acetate (2×200 ml) then washed with aqueous sodium bicarbonate (100 ml) and saturated brine (100 ml). The solution was dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo to afford the title compound as a dark solid (4.4 g).

Provenance & Evidence