Methyl vinyl ketone → HCID 23362108, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,3-dichlorobenzenamine monohydrochloride (0.308 mol), iron(III) chloride (0.52 mol) and zinc chloride (0.0308 mol) in ethanol (800 ml) was heated at 65° C. for 30 minutes. 3-butenone (0.308 mol) in ethanol (200 ml) was added dropwise at 65° C. over a 1 hour period and the mixture was stirred and refluxed overnight. The mixture was cooled to room temperature and evaporated. The residue was taken up in water, basified with NH4OH, filtered off and extracted with ethyl acetate. The organic layer was extracted with 3N HCl. The aqueous layer was basified with NH4OH and extracted with ethyl acetate. The organic layer was dried (MgSO4) and evaporated, yielding 38g (58%) of 7,8-dichloro-4-methylquinoline (interm. 1).

Provenance & Evidence