4-Chloro-8-(trifluoromethyl)quinoline → Methyl 2-(8-trifluoromethyl-4-quinolinylamino)-5-fluoro-benzoate

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Reaction Steps

A solution of 16 g of 4-chloro-8-trifluoromethylquinoline, 11.62 g of methyl 2-amino-5-fluoro-benzoate and 70 ml of 2 N hydrochloric acid solution was heated to reflux and was allowed to stand overnight at room temperature. The mixture was iced and filtered and the product was empasted with a little water and was vacuum filtered. The recovered crystals were dissolved in methanol and triethylamine was added to the resulting solution until the pH was alkaline. The mixture was iced and filtered and the product was dried to obtain 11.2 g of methyl 2-(8-trifluoromethyl-4-quinolinylamino)-5-fluoro-benzoate melting at 166° C.

Provenance & Evidence