2,4-Dichloro-5-methoxyaniline → HCID 23498103, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-7-fluoro-6-(2-methoxyethoxy)-3-quinolinecarbonitrile (1.00 g, 3.59 mmol), 2,4-dichloro-5-methoxyaniline (727 mg, 3.77 mmol) and pyridine hydrochloride (620 mg, 5.34 mmol) in 18 mL of 2-ethoxyethanol is heated at 100-105° C. for 2 hours. The reaction mixture is cooled to room temperature and then poured into ice cold saturated sodium bicarbonate. The solids are collected, washed with water and then treated with methanol and dichloromethane. The mixture is filtered and the filtrate is concentrated. The solid residue is slurried with hexane, and the solids are collected by filtration to provide 1.15 g of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-fluoro-6-(2-methoxyethoxy)-3-quinolinecarbonitrile, mp 170-172° C.

Provenance & Evidence