Thionyl Chloride → 3-(chloromethyl)-N-ethyl-6-methoxyquinolin-2-amine

Participants

Reaction Steps

To a stirred solution of (2-(ethylamino)-6-methoxyquinolin-3-yl)methanol SLA 28164 (1.150 g, 4.95 mmol) in dry CH2Cl2 (127 mL) a 250 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (7.18 mL, 99.0 mmol). The mixture was stirred for 2 h at RT then concentrated to dryness at 40° C. under vacuum. The residue was taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times) to give 3-(chloromethyl)-N-ethyl-6-methoxyquinolin-2-amine hydrochloride SLA 28166 as a yellow solid (1.43 g, 100% yield) that was used immediately in the next step.

Provenance & Evidence