Sodium bis(trimethylsilyl)amide → HCID 67726448, compound

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Reaction Steps

2.2 g (5.31 mmol) of 4,6-dichloro-N-[3-(pyrimidin-5-yl)-propylthio]acetyl-anthranilic acid methyl ester are placed in 25 ml of tetrahydrofuran at 0° under nitrogen. 10.62 ml of a 1-molar tetrahydrofuran solution of sodium bis-trimethylsilylamide are added dropwise thereto. The mixture is then stirred for 2 hours at 0°. The reaction mixture is poured into 50 ml of 2N hydrochloric acid/ice and filtered. 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, washed with hexane and dried. 1.75 g (86.2% of theory) of 5,7-dichloro-4-hydroxy-3-[3-(pyrimidin-5-yl)propylthio)-2-(1H)-quinolone are obtained in the form of red crystals having a melting point of 252°-254°.

Provenance & Evidence