Thionyl Chloride → 3-(Chloromethyl)-6-methoxy-N-propylquinolin-2-amine hydrochloride

Participants

Reaction Steps

To a stirred solution of (6-methoxy-2-(propylamino)quinolin-3-yl)methanol SLA 28174 (1.45 g, 5.88 mmol) in dry CH2Cl2 (115 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (8.53 mL, 118 mmol). The mixture was stirred for 2 h at RT then concentrated to dryness at 40° C. under vacuum. The residue was then taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times), to give 3-(chloromethyl)-6-methoxy-N-propylquinolin-2-amine hydrochloride SLA 28178 (1.28 g, 82% yield) as a yellow solid.

Provenance & Evidence