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

Participants

Reaction Steps

To a solution of 2-[2-(3-bromophenyl)-acetylamino]-4-chloro-5-nitro-benzoic acid methyl ester (1.18 g in 15 mL dry tetrahydrofuran) at 0° C. was added dropwise a solution of sodium bis(trimethylsilyl)amide (6.9 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 200 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 (887 mg).

Provenance & Evidence