2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 21449334, compound

Participants

Reaction Steps

A solution of methyl 1-(7-chlorocinnolin-4-yl)-5-methoxy-2-methylindolin-3-ylacetate (7.9g.) in dry 1,2-dimethoxyethane [80ml.; dried over sodium alumino-silicate (molecular sieve type 4A; obtainable from BDH Chemicals Ltd., Poole, England)] was mixed with a solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (4.5g.) in dry 1,2-dimethoxyethane (30ml.). The solution was heated under reflux for 20 minutes and then evaporated in vacuo. The residue was extracted with chloroform (5 × 50ml.). Evaporation of the extracts gave an oil, which was purified by chromatography on silica gel (350g.), using ether as eluant, to give methyl 1-(7-chlorocinnolin-4-yl)-5-methoxy-2-methylindol-3-ylacetate as a red syrup, homogeneous by thin layer chromatography (ether: silica gel) [hereinafter referred to as system C], and having a satisfactory NMR spectrum (5-OCH3, τ6.13).

Provenance & Evidence