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

Participants

Reaction Steps

To a stirred solution of (6-methoxy-2-(2-methoxyethylamino)quinolin-3-yl)methanol SLA 47064A (0.90 g, 3.43 mmol) in dry CH2Cl2 (30 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (4.98 mL, 68.6 mmol). The mixture was stirred for 1.5 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-(2-methoxyethyl)quinolin-2-amine hydrochloride SLA 47064 as a yellow solid (1.13 g, 100%).

Provenance & Evidence