Thionyl Chloride → 4-(Chloromethyl)quinoline--hydrogen chloride (1/1)

Participants

Reaction Steps

To a solution of quinolin-4-ylmethanol MDE 32014 (0.28 g, 1.76 mmol) in dry CH2Cl2 (18 mL) at 0° C. under N2 in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (2.6 mL, 36.0 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 4-(chloromethyl)quinoline hydrochloride MDE 32016 as an off-white solid (246 mg, 65% yield).

Provenance & Evidence