Epichlorohydrin → 5-(Oxiran-2-ylmethoxy)quinoline

Participants

Reaction Conditions

Reaction Steps

83 g of 5-hydroxyquinoline were dissolved in 1.5 l of dried dimethylformamide (DMF), and, after adding 23.3 g of sodium hydride (content: 60% ), the resulting mixture was stirred with heating at 50° C. for 30 minutes. 160 g of epichlorohydrin were added to the reaction mixture, and, after stirring with heating at 90° C. for 3 hours, the solvent was evaporated off under reduced pressure. Water was added to the resulting residue and extracted with chloroform. The chloroform extract was decolorized and purified with active carbon, dried with anhydrous mirabilite and then evaporated. The residue was purified by column chromatography on silica gel. 71 g of the targeted 5-(2,3-epoxypropoxy)quinoline were obtained as an oily substance by chromatography using a solvent mixture of chloroform:methanol=100:1 (volume ratio)for elution.

Provenance & Evidence