39885-08-0

General procedure for the synthesis of (2-amino-6-chlorophenyl)-methanol from 2-amino-6-chlorobenzoic acid: 50.0 g (286 mmol) of 2-amino-6-chlorobenzoic acid was dissolved in 300 mL of anhydrous tetrahydrofuran (THF). The resulting solution was cooled to 0-10°C, followed by the slow addition of 450 mL of 1.0 M lithium aluminum hydride in THF solution. The reaction mixture was gradually warmed to room temperature and stirred continuously at room temperature overnight. Upon completion of the reaction, 300 mL of 10% aqueous sodium hydroxide solution was carefully added to the mixture to quench the reaction. The organic phase was separated and washed sequentially with ethyl acetate and water. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent, yielding 42 g (270 mmol, 95% yield) of a yellow solid product, which could be used without further purification.

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