Thionyl Chloride → 3-(Chloromethyl)-7-methoxyquinoline hydrochloride

Participants

Reaction Steps

To a solution of (7-methoxyquinolin-3-yl)methanol MDE 32006 (219 mg, 1.16 mmol) in dry CH2Cl2 (12 mL) at 0° C. under N2 in a 25 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (1.68 mL, 23.16 mmol) and the mixture was stirred for 1 h at RT. The volatiles were then removed at 40° C. under vacuum and the residue was taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times) to give 3-(chloromethyl)-7-methoxyquinoline hydrochloride MDE 32012 as an off-white solid (246 mg, 87% yield).

Provenance & Evidence