Chloranil → HCID 21449365, compound

Participants

Reaction Steps

A mixture of ethyl 1-(7-chloroquinol-4-yl)-5-methoxy-2-methylindolin-3-ylacetate (7.0g.) and 2,3,5,6-tetrachloro-1,4-benzoquinone (5.6g.) in dry xylene (50ml.) was heated under reflux for 1.5 hours. The mixture was then cooled and filtered. The filtrate was washed successively with cold 2N-sodium hydroxide solution (2 × 30ml.) and water (2 × 50ml.). The organic layer was dried (MgSO4) and evaporated in vacuo to dryness, and the residue (dissolved in the minimum volume of diethyl ether) was adsorbed on a column of chromatographic silica gel (column dimensions: 15 × 3.5cm.). The column was eluted with a 1:3 v/v mixture of diethyl ether and petroleum ether (b.p. 40°-60° C.), and the eluate was evaporated in vacuo to give ethyl 1-(7-chloroquinol-4-yl)-5-methoxy-2-methylindol-3-ylacetate as a yellow oil, NMR: -OCH3, τ6.12.

Provenance & Evidence