Anthranilic Acid → 1,4-Dihydro-1,4-epoxynaphthalene

Participants

Reaction Steps

Solutions of 20 ml of isoamyl nitrite in glyme (20 ml) and of 13.7 g of anthranilic acid in glyme (45 ml) were added simultaneously by drops to a refluxing mixture of glyme (50 ml) and furan (50 ml). Refluxing was continued for ten minutes and the brown solution was cooled, made basic with aqueous sodium hydroxide (1 N), and extracted with petroleum ether. The extract was washed thoroughly with water, clarified with Norit®, dried, and evaporated to give an oil. The oil solidified on cooling to give 7 g (51% yield) of light yellow solid. Recrystalization of the yellow solid from petroleum ether gave colorless crystalline solid of 1,4-dihydronaphthalene-1,4-endo-oxide (IIIa), m.p. 53°-54° C. (lit. m. p. 56° C.).

Provenance & Evidence