5-Chloro-8-hydroxyquinoline → HCID 54052186, compound

Participants

Reaction Steps

3.6 g (0.09 mol) of NaOH pellets are dissolved in 300 ml of water, and 300 ml of methylene chloride are added; there are subsequently added 10.8 g (0.06 mol) of 5-chloro-8-oxyquinoline, 16.2 g of 2-butenyl bromide (0.12 mol) and 0.5 g of tetra-n-butylammonium bromide, and the mixture is stirred for 5 hours at room temperature. The organic layer is separated, and the aqueous layer is extracted twice with methylene chloride. The organic solvents are combined and concentrated by evaporation. The residue is taken up in water and methylene chloride; the organic layer is then extracted by shaking three times with 2N NaOH, separated, dried with Na2SO4 and concentrated by evaporation; crude yield 15.5 g.

Provenance & Evidence