Dichloromethane → 5-(Chloromethyl)isoquinoline hydrochloride

Participants

Reaction Steps

To a solution of isoquinolin-5-ylmethanol MDE 32040 (0.53 g, 3.33 mmol) in dry CH2Cl2 (10 mL) at 0° C. under N2 in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (4.9 mL, 67.4 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 5-(chloromethyl)quinoline hydrochloride MDE 32044 as an off-white solid (301 mg, 42% yield).

Provenance & Evidence