Sulfuric Acid → 4,7-Dimethylquinoline

Participants

Reaction Conditions

Reaction Steps

A solution of 3-methyl-phenylamine (1 eq), in 1,4-dioxane is stirred and cooled to approximately 12° C. Sulfuric acid (2 eq.) is slowly added and heated at reflux. Methylvinyl ketone (1.5 eq) is added dropwise into the refluxing solution. The solution is heated for 1 h after addition is complete. The reaction solution is evaporated to dryness and dissolved in methylene chloride. The solution is adjusted to pH 8 with 1 M sodium carbonate and extracted with three times with water. The residue is chromatographed on SiO2 (70/30 hexane/ethylacetate) to yield the title compound.

Provenance & Evidence