Thionyl Chloride → N-(2-(3-(Chloromethyl)-6-(cyclopropylmethoxy)quinolin-2-ylamino)ethyl)acetamide hydrochloride

Participants

Reaction Steps

To a stirred solution of N-(2-(6-(cyclopropylmethoxy)-3-(hydroxymethyl)quinolin-2-ylamino)ethyl)acetamide SLA 47096A (0.374 g, 1.1 mmol) in dry CH2Cl2 (11 mL) in a 25 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (1.65 mL, 22.7 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 N-(2-(3-(chloromethyl)-6-(cyclopropylmethoxy)quinolin-2-ylamino)ethyl)acetamide hydrochloride SLA 47096B as a yellow solid (0.475 g, 100% yield).

Provenance & Evidence