Sodium bis(trimethylsilyl)amide → 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-1H-quinolin-2-one

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Reaction Steps

To a solution of 4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-benzoic acid methyl ester (3.05 g in 20 mL dry tetrahydrofuran) at 0° C. was added dropwise a solution of sodium bis(trimethylsilyl)amide (20 mL of a 1.0M solution in tetrahydrofuran) and the mixture warmed to room temperature. After 2 hours, the reaction was cooled to 0° C. and quenched by the addition of 100 mL iced 6N hydrochloric acid. The slurry was stirred for 15 minutes then filtered and washed (2×) with ice cold acetonitrile. The residue was dried in vacuo overnight to give the title compound (2.3 g).

Provenance & Evidence