Benzoic acid, 4-amino-3-chloro-5-[(methoxyimino)methyl]-, methyl ester → 4-Amino-3-chloro-5-methoxyiminomethylbenzoic acid

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The methyl 4-amino-3-chloro-5-methoxyiminomethylbenzoate made in the previous step was dissolved in a mixture of 25 ml of methanol and 8 g ml of 10% of aqueous sodium hydroxide and the solution was then was refluxed for 2 hours. The methanol was removed using a rotary evaporator and the residue was partitioned between 25 ml of water and 25 ml of methylene chloride. To the cooled aqueous layer was added 6N aqueous hydrochloric acid, dropwise, with stirring, until the pH of mixture reached a value of 1. The resulting solid was filtered and dried yielding 1.4 g 4-amino-3-chloro-5-methoxyiminomethylbenzoic acid used without further purification.

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