Water → HCID 19867092, compound

Participants

Reaction Steps

n-Butyllithium (17.5 cm3 of a 1.5M solution in n-hexane) was added dropwise to a stirred solution of 6-(5-chloro-4-cyano-2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone (3.57 g) in tetrahydrofuran (THF) (100 cm3) at -70° under nitrogen. After 15 minutes saturated aqueous ammonium chloride solution (20 cm3) was added and the mixture was warmed to room temperature over 1 hour. The mixture was then poured into water (50 cm3), extracted with ethyl acetate (4×150 cm3), and the combined and dried (MgSO4) organic extracts were evaporated in vacuo to give a residue which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]). Elution with methanol:dichloromethane, 1:19 by volume, followed by combination and evaporation of the appropriate fractions, gave a solid which was boiled with ethyl acetate/methanol, then filtered and dried to afford the title compound, (0.71 g), which was shown spectroscopically to be identical to the product of Preparation 2.

Provenance & Evidence