Sodium bis(trimethylsilyl)amide → HCID 54735472, compound

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Reaction Steps

0.55 g (1.3 mmol) of 4-chloro-6-nitro-N-(3-phenylpropylthio)acetyl-anthranilic acid methyl ester are placed in 6 ml of tetrahydrofuran at 0° under nitrogen. 2.6 ml of a 1-molar tetrahydrofuran solution of sodium bis-trimethylsilylamide are added dropwise thereto. The mixture is then stirred for 1 hour at 0°. The reaction mixture is poured into 50 ml of 2N hydrochloric acid/ice and extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated by evaporation. The residue is taken up in a small amount of ethyl acetate, and hexane is added until precipitation begins. The precipitate formed is filtered off with suction and dried. 374 mg (73% of theory) of 7-chloro-5-nitro-4-hydroxy-3-(3-phenylpropylthio)-2(1H)-quinolone are obtained in the form of red crystals having a melting point of 177°-184°.

Provenance & Evidence