Thionyl Chloride → 3-(chloromethyl)-6-methoxy-N-methylquinolin-2-amine hydrochloride

Participants

Reaction Steps

To a stirred solution of (6-methoxy-2-(methylamino)quinolin-3-yl)methanol SLA 28152 (0.906 g, 4.15 mmol) in dry CH2Cl2 (100 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (6.03 mL, 83.1 mmol). The mixture was stirred for 1 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-methylquinolin-2-amine hydrochloride SLA 28154 (1.20 g, >100%) as a yellow solid.

Provenance & Evidence