Hydrogen Bromide → 1-(2-Propen-1-yl)-1,8-naphthyridine-2,7(1H,8H)-dione

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(2-propen-1-yl)-7-(2-propen-1-yloxy)-1,8-naphthyridin-2(1H)-one (440 mg, 1.8 mmol) in acetic acid (1 ml) was treated with 33% hydrogen bromide in acetic acid (1 ml) and heated for 1 hour at 50° C. and 10 hours at 80° C. The mixture was evaporated to dryness and taken to pH4 with saturated aqueous sodium bicarbonate (˜5 ml). The mixture was extracted with ethyl acetate, dried and evaporated. The residue was chromatographed eluting with 0-100% ethyl acetate in hexane affording the product as a yellow oil (123 mg, 34%).

Provenance & Evidence