Methyl iodide → 4-Bromo-1-methylpyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of 4-bromopyridin-2-amine (600 mg, 3.5 mmol) in a mixture of 2M H2SO4 (20 mL) and 2M Na2NO2 (10 mL) was stirred at 0-5° C. for 2 h. The reaction mixture was extracted with CH2Cl2, and the organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated. The crude product was used in next step without further purification. The crude product 15a, potassium carbonate (3.6 mmol) and methyl iodide (3.7 mmol) were refluxed in acetone (100 mL) in a sealed tube for 4 h. The reaction mixture was cooled, and potassium carbonate was filtered off. The acetone was evaporated off and a small amount of water was added to the residue. This solution was extracted with CH2Cl2. The organic layer was dried, concentrated and purified with column chromatography to afforded 17a (355 mg, 57%). 1H NMR (CDCl3,): δ 3.49 (s, 3H), 6.31 (d, J=6.0 Hz, 1H), 6.82 (s, 1H), 7.14 (d, J=6.0 Hz, 1H).

Provenance & Evidence