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

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Reaction Steps

To a solution of 4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-iodo-benzoic acid methyl ester (EXAMPLE 4.1B, 10.9 g in 180 mL dry tetrahydrofuran) at 0° C. was added dropwise 59.5 mL of a 1 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran and the mixture allowed to warm to room temperature. After 1.5 hours, the mixture was cooled to 0° C. and the reaction quenched by the addition of 400 mL ice:6N hydrochloric acid (1:1). This was stirred for 15 minutes then filtered to collect the solid product. The solids were washed with ice-water then cold acetonitrile and dried to give the title compound (9.8 g).

Provenance & Evidence