Water → HCID 136023069, compound

Participants

Reaction Steps

To a solution of 4-(3,4-diisopropoxyphenyl)-6-isopropoxy-7-methoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylic acid ethyl ester (96.0 mg) in dichloromethane (1.0 ml), titanium tetrachloride (TiCl4) (316 mg) was added at 0° C., followed by stirring at the same temperature for 10 hours. The reaction mixture was poured over water and extracted with ethyl acetate. The ethyl acetate layer was washed by sequential additions of a saturated aqueous sodium hydrogen carbonate solution and water and then dried (MgSO4), after which the solvent was distilled off. The residual oily substance was subjected to silica gel column chromatography and eluted with ethyl acetate-methanol (10:1, v/v) to yield 4-(3,4-dihydroxyphenyl)-6-hydroxy-7-methoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylic acid ethyl ester (19.0 mg, 26%) having a melting point of 264° to 266° C.

Provenance & Evidence