Methyl iodide → 3,5-Dimethoxy-N-methylbenzenamine

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[NH2:6].IC.[C:14]([O-])(=O)C.[Na+]>C1COCC1>[CH3:11][O:10][C:8]1[CH:7]=[C:5]([NH:6][CH3:14])[CH:4]=[C:3]([O:2][CH3:1])[CH:9]=1

Participants

Procedure

A solution of 3,5-dimethoxyaniline (13.8 g, 90 mmol), Iodomethane (12.7 g, 90 mmol), and sodium acetate (7.4 g, 90 mmol) in 100 ml of anhydrous THF was stirred under nitrogen atmosphere for 10 hr. Then, THF was removed by rotary evaporation. The crude product was partitioned between water and ethyl ether. The ethereal extraction was separated and washed with water, brine, and dried over Na2SO4. Filtration and removal of solvent provided 13.6 g of crude product. The crude product was chromatographed on silica gel (33% acetone-petroleum ether) to afford the expected product 4.5 g (27% yield).