Sodium bis(trimethylsilyl)amide → HCID 54678918, compound

Participants

Reaction Steps

2 g (5.3 mmol) of 4-chloro-N-(3-phenylpropylthio)acetyl-anthranilic acid methyl ester are placed in 20 ml of tetrahydrofuran at 0°. A 1-molar tetrahydrofuran solution of sodium bis-trimethylsilylamide is added dropwise thereto. The mixture is then stirred for 20 minutes at 0° and for 2 hours at room temperature. The reaction mixture is poured into 200 ml of 2N hydrochloric acid/ice and the resulting white suspension is filtered off. The resulting colourless crystals are made into a suspension in ethanol and stirred for 2 hours. The mixture is filtered, followed by washing with ethanol and diethyl ether. After drying, 7-chloro-4-hydroxy-3-(3-phenylpropylthio)-2(1H)-quinolone is obtained in the form of colourless crystals having a melting point of 184°-186°.

Provenance & Evidence