Thionyl Chloride → 3-(Chloromethyl)quinoline hydrochloride

Participants

Reaction Steps

To a solution of quinolin-3-ylmethanol MDE 32002 (0.26 g, 1.63 mmol) in dry CH2Cl2 (10 mL) at 0° C. under N2 in a 25 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (2.4 mL, 33.1 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)quinoline hydrochloride MDE 32004 as an off-white solid (301 mg, 85% yield).

Provenance & Evidence