Methyl iodide → HCID 59740586, compound

Participants

Reaction Steps

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was charged with 5-(2-methyl-3-nitrophenyl)pyridin-2-one (9) (0.92 g, 4.0 mmol), DMF (40 mL), potassium carbonate (1.21 g, 8.80 mmol) and iodomethane (625 mg, 4.40 mmol) and purged with nitrogen. The reaction mixture was stirred at room temperature for 2 h. After this time the reaction was cooled to room temperature and partitioned between ethyl acetate (150 mL) and water (75 mL). The organic layer was separated and washed with water (2×50 mL) followed by brine (100 mL) and dried over magnesium sulfate. The drying agent was then removed by filtration and the filtrate concentrated under reduced pressure to afford 0.92 g (94%) of 1-methyl-5-(2-methyl-3-nitrophenyl)pyridin-2-one (10) as a white solid: mp 157-159° C.; 1H NMR (300 MHz, CDCl3) 7.81 (dd, 1H, J=7.8, 1.8 Hz), 7.41 (dd, 1H, J=7.8, 1.8 Hz), 7.38 (d, 1H, J=7.5 Hz), 7.53 (d, 1H, J=9.3 Hz), 7.32 (dd, 1H, J=9.3, 2.7 Hz), 7.27 (d, 1H, J=1.5 Hz), 6.68 (d, 1H, J=9.3 Hz), 3.62 (s, 3H), 2.37 (s, 3H); MS (ESI+) m/z 245 (M+H).

Provenance & Evidence