Methyl iodide → N-(7-methoxynaphthalen-1-yl)acetamide

Participants

Reaction Steps

To a mixture of N-(7-hydroxynaphthyl)acetamide (175.4 g, 0.872 mol), potassium carbonate (301 g, 2.18 mol), and acetone (1 l) was added iodomethane (270 mL, 4.36 mol). The reaction mixture was refluxed for 6 hr, cooled to room temperature, and the solvent removed. The residue was filtered through silica with ethyl acetate and triturated with ethyl acetate to yield 161.6 g (86%) of a gray solid. An analytical sample was further purified by preparative reverse phase HPLC to yield the title compound as a white solid: mp 154-155° C.; 1H NMR (DMSO-d6): δ 2.19 (3H, s), 3.90 (3H, s), 7.19 (1H, dd, J=2.39 Hz, J=8.94 Hz), 7.29-7.34 (2H, m), 7.39 (1H; d, J=1.86 Hz), 7.75-7.68 (2H, m), 7.87 (1H, d, J=8.96 Hz), 9.82 (1H, s); MS (ESI) m/z 216 (M+H)+.

Provenance & Evidence