Acetic Acid → 6-Iodoquinoxaline

Participants

Reaction Steps

A solution of 4-iodo-benzene-1,2-diamine (0.46 g, 1.96 mmol), ethanedial [40% in water] (2.25 mL), acetic acid (1 mL) and ethanol (20 mL) were heated to 100° C. for several hours and then cooled to room temperature. Water was added and the crude product was extracted with ethyl acetate. The product was purified via silica gel column chromatography with hexane:ethyl acetate (1:1) to give 0.323 g (64%) of 6-iodo-quinoxaline. 1H NMR (400 MHz, CDCl3) δ 8.77 (dd, 2H, J=2.0, 8.8 Hz), 8.46 (d, 1H, 2.0 Hz), 7.96 (dd, 1H, J=2.0, 8.8 Hz), 7.75 (d, 1H, J=8.8 Hz).

Provenance & Evidence