Selenium Dioxide → 1,8-Naphthyridine-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

4-Methyl-[1,8]naphthyridine (0.743 g, 5.15 mmol) was dissolved in dioxane (32 mL) and water (4 mL). Selenium dioxide (1.14 g, 103 mmol) was added, and the solution was heated to 80° C. for 1 h. Subsequently more selenium dioxide (0.020 g, 1.80 mmol) was added, the solution heated for 30 min, and then allowed to cool to RT. The solution was passed through a syringe filter to remove solids, and poured into a solution of water : satd. aq. NaHCO3 (1:1) (60 mL). The organic layer was separated and the remaining aqueous extracted with DCM (2×100 mL) and (1×50 mL). The organic fractions were combined, dried over Na2SO4, filtered, and concentrated under vacuum. The product was purified (SGC using MeCN:hexanes in 1:1 ratio) to yield the title compound (0.63 g). MS (ESI+) for m/z 159 (M+H)+. 1H NMR (CDCl3) δ 10.39 (s, 1H), 9.39-9.37 (m, 2H), 9.16 (d, 1H), 7.85 (d, 1H), 7.61 (dd, 1H).

Provenance & Evidence