Sodium bis(trimethylsilyl)amide → 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-nitro-1H-quinolin-2-one

Participants

Reaction Steps

To a solution of 4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-nitrobenzoic acid methyl ester (1.17 g in 10 mL dry tetrahydrofuran) at 0° C. was added dropwise a solution of sodium bis(trimethylsilyl)amide (7.8 mL of a 1.0M solution in tetrahydrofuran) and the mixture warmed to room temperature. After 2 hours, the reaction was quenched by the addition of 100 mL iced 6N hydrochloric acid. The slurry was stirred for 10 minutes then filtered and washed (2×) with ice water and then cold acetonitrile. The residue was dried overnight at 45° C. to give the title compound (970 mg).

Provenance & Evidence