Hydrochloric Acid → 4-{[1-(5-Chloro-3-methyl-1-benzofuran-2-yl)-3-methylbutyl]amino}benzoic acid

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Reaction Conditions

Reaction Steps

To a mixture of 5-chloro-2-(1-chloro-3-methylbutyl)-3-methyl-1-benzofuran (668 mg) synthesized above, methyl 4-aminobenzoate (410 mg), sodium iodide (737 mg) and N,N-dimethylformamide (10 mL) was added sodium carbonate (521 mg) and the mixture was stirred at 80° C. for 8 hr. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (15% ethyl acetate/hexane) to give a yellow oil. To a mixture of the obtained oil, tetrahydrofuran (10 mL) and ethanol (10 mL) was added 1N aqueous sodium hydroxide solution (10.0 mL), and the mixture was stirred with heating under reflux for 8 hr, and concentrated under reduced pressure. The residue was dissolved in water (20 mL), and 1N hydrochloric acid (10.0 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title object compound (394 mg, 43%) as a pale-yellow solid.

Provenance & Evidence