Thionyl Chloride → 3-(Chloromethyl)-N-isopropyl-6-methoxyquinolin-2-amine hydrochloride

Participants

Reaction Steps

To a stirred solution of (2-(isopropylamino)-6-methoxyquinolin-3-yl)methanol SLA 28188 (1.41 g, 5.72 mmol) in dry CH2Cl2 (115 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (8.30 mL, 114 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)-N-isopropyl-6-methoxyquinolin-2-amine hydrochloride SLA 28190 as a yellow solid (1.79 g, >100% yield).

Provenance & Evidence