Dichloromethane → 4-Chloro-6-iodo-2-methoxy-3-(4-methylbenzyl)quinoline

Participants

Reaction Conditions

Reaction Steps

Sodium methoxide (3.2 g, 60 mmol) was added to a solution of 2,4-dichloro-6-iodo-3-(4-methylbenzyl)quinoline (4.3 g, 10 mmol, Intermediate 22: step b) in toluene (50 mL) with stirring. The mixture was heated to 105° C. After 18 hours, the flask was allowed to cool to 23° C. Dichloromethane (100 mL) was added and then the mixture was filtered through Celite®. The filter cake was washed with dichloromethane. The filtrate was concentrated and the residue was purified by flash column chromatography on silica gel eluting with hexanes initially, grading to 20% ethyl acetate-hexanes to provide the title compound as a white solid.

Provenance & Evidence