Hydrochloric Acid → 5-[5-(3,4-dichlorobenzoylamino)pyridin-2-yloxy]-1H-indole-2-carboxylic acid

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Reaction Steps

5-[5-(3,4-Dichlorobenzoylamino)pyridin-2-yloxy]-1H-indole-2-carboxylic acid methyl ester (1.00 g, 2.19 mmol) was dissolved in THF (30 mL). To the solution were added 1 M sodium hydroxide (3.50 mL, 3.50 mmol) and water (15 ml), and the resulting solution was refluxed for 3 hours. After cooling with ice, 1 M hydrochloric acid (3.50 mL, 3.50 mmol) and brine (50 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (30 ml). After the organic layer was washed with brine, then dried over anhydrous sodium sulfate, the solvent was evaporated. The obtained residue was crystallized from n-hexane to yield 0.875 g of the title compound as a pale yellow powder.

Provenance & Evidence