Chlorosuccinimide → 4-Chloro-2-methyl-2,6-naphthyridin-1-one

Participants

Reaction Conditions

Reaction Steps

N-chlorosuccinimide (0.8 g, 6.2 mmol) was added in portions to a solution of 2-methyl-2,6-naphthyridin-1-one (1.0 g, 6.2 mmol) in acetonitrile (25 mL) which was then heated at 65° C. for 18 h. Extractive work up with ethyl acetate and purification by silica gel chromatography (PE:EA=5:1-1:1) gave the title compound of step 1 (0.6 g, 56%) as a yellow solid. 1H NMR: (CDCl3, 400 MHz) δ 9.29 (s, 1H), 8.81 (d, J=3.6 Hz, 1H), 8.21 (d, J=5.2 Hz, 1H), 7.31 (s, 1H), 3.63 (s, 3H). LCMS: 195.0 (M+H)+.

Provenance & Evidence