Methyl iodide → 7-Fluoro-2-methylisoquinolin-1(2H)-one

Participants

Reaction Conditions

Reaction Steps

Under N2, sodium hydride (710 mg, 29.4 mmol) was added to 7-fluoro-2H-isoquinolin-1-one (4 g, 24.55 mmol) in dry DMF (40 mL) at 0° C. After stirring at 0° C. for 20 min, CH3I (5.2 g, 36.7 mmol) was added. The mixture was stirred at 26° C. for 2 h. Saturated aqueous NH4Cl (20 mL) was added and after extractive work up with ethyl acetate, purification by silica gel chromatography (PE:EA=10:1) gave the title compound (2.2 g, 50%) as an off-white solid. 1H NMR (CDCl3, 400 MHz) δ 8.06 (dd, J1=9.6 Hz, J2=2.8 Hz, 1H), 7.50 (dd, J1=8.8 Hz, J2=5.2 Hz, 1H), 7.38-7.36 (m, 1H), 7.03 (d, J=7.6 Hz, 1H), 6.48 (d, J=7.2 Hz, 1H), 3.61 (s, 3H). LCMS: 178.1 [M+H]+

Provenance & Evidence