Water → 4-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester

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Reaction Steps

A suspension of 60% sodium hydride/oil dispersion (1.00 g, 0.025 mole) in anhydrous dimethylformamide (40 ml) under nitrogen was treated with 4-amino-5-chloro-2-hydroxybenzoic acid, methyl ester (4.03 g, 0.020 mole), stirred for 30 minutes, then treated with 2-bromoethyl methyl ether (3.48 g, 0.025 mole). The mixture was heated to 95°±5° C. for 1.5 hours, then cooled and added to water (250 ml). The aqueous suspension was filtered, and the solid was washed with water, air dried, collected, and recrystallized from ether/hexane to afford 2.75 g (53%) of 4-amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester; mp 121.0°-122.5° C.

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