Sodium bis(trimethylsilyl)amide → HCID 54737669, compound

Participants

Reaction Steps

2.0 g (5.6 mmol) of 4-chloro-N-(3-methoxycarbonylpropylthio)acetyl-anthranilic acid methyl ester are placed in 20 ml of tetrahydrofuran at 0° , and 16.8 ml of a 1M solution of sodium bis-trimethylsilylamide are added dropwise thereto. The mixture is then stirred for 30 minutes at 0° and the reaction mixture Is then poured into 2N hydrochloric acid/ice. The resulting white suspension is filtered with suction and the resulting colourless crystals are dried under a high vacuum at 60°. The dried product is made into a suspension in ethyl acetate and stirred for 30 minutes. The suspension is filtered, and the colourless crystals are dried under a high vacuum at 70°, yielding 7-chloro-4-hydroxy-3-(3-methoxycarbonyl-propylthio)-2(1H)-quinolone in the form of colourless crystals having a melting point of 183°-185° (decomp.).

Provenance & Evidence