Water → HCID 53823228, compound

Participants

Reaction Steps

Anhydrous sodium acetate (3.6 g.) was added to a mixture of methyl 5-methoxy-2-methylindolin-3-ylacetate (8.0 g.) and 2,3-dichloroquinoxaline (6.8 g.) in diethyleneglycol dimethyl ether (150 ml.), and the mixture was heated under reflux for 12 hrs. The mixture was then cooled and poured into water (800 ml.), and the aqueous suspension was extracted with ethyl acetate (3 × 50 ml.). The combined extracts were washed successively with water (4 × 30 ml.) and a saturated aqueous solution of sodium chloride (50 ml.), and then dried (MgSO4) and evaporated. The resultant syrup was chromatographed on chromatographic silica gel (M.F.C., 300 g.) using an increasing gradient of diethyl ether in petroleum ether (b.p. 40°-60° C.) (polarity increased by incremental addition of 10% v/v ether.) The combined eluate was evaporated to give methyl 1-(3-chloroquinoxalin-2-yl)-5-methoxy-2-methylindolin-3-ylacetate, m.p. 155°-157° C.

Provenance & Evidence