Potassium Hydroxide → 3-[(Furan-2-yl-methyl)-amino]-phtalic acid

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Reaction Steps

To a stirred solution of crude 3-[(furan-2-yl-methyl)-amino]-phthalic acid dimethyl ester in methanol (100 ml), was added 5N potassium hydroxide (79 ml). The mixture was stirred at room temperature overnight. The solvent was evaporated in vacuo and the residue dissolved in water (50 ml). The water was washed with diethyl ether (2×100 ml). The aqueous portion was cooled in an ice bath and the pH was adjusted to 2-3 by dropwise addition of concentrated hydrochloric acid. The aqueous solution was then extracted into ethyl acetate (3×100 ml). The combined ethyl acetate extracts were washed with brine (150 ml), and dried over MgSO4. The solvent was evaporated in vacuo, and the residue, which contained a mixture of diacid and monomethyl esters, was used without further purification.

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