Iodine → 6-chloro-3-iodo-7-methoxy-2-methylquinolin-4(1H)-one

Participants

Reaction Steps

To a stirred solution of 6-chloro-7-methoxy-2-methylquinolin-4(1H)-one (6.43 g, 28.7 mmol) and n-butylamine (28 ml, 287 mmol) in dimethylformamide (57 ml) cooled by a room temperature water bath was added iodine (7.30 g, 28.7 mmol) in a saturated solution of aqueous potassium iodide (29 ml). The reaction mixture was stirred 12 hours at room temperature. Residual iodine was quenched with 0.1 M aqueous sodium thiosulfate, and the resulting solution was concentrated in vacuo. The residue was resuspended in water and filtered to give 8.93 g (89% yield) of 6-chloro-3-iodo-7-methoxy-2-methylquinolin-4(1H)-one as a light brown powder. 1H NMR (400 MHz, DMSO-d6) δ 11.65 (bs, 1H), 7.59 (s, 1H), 6.41 (s, 1H), 3.91 (s, 3H), 2.18 (s, 3H).

Provenance & Evidence