Methanol → HCID 21931673, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.63 g (3.5 mmol) 3-methoxy-6-nitro-2-vinyl-pyridine in 50 ml of CH2Cl2 and 10 ml of methanol was cooled to −70° C. Ozone was bubbled into the solution until a blue color persisted. The mixture was stirred for 60 minutes at −70° C. and then quenched with excess dimethyl sulfide. The reaction was warmed to room temperature and the solvent evaporated. The residue was dissolved in ethyl acetate and water. The pH of the solution was adjusted to 2.0 with 1N HCl and the mixture stirred for 30 minutes. The pH of the solution was then adjusted to 8.0 with 1N NaOH. The mixture was extracted with excess ethyl acetate. The ethyl acetate extracts were combined, dried (Na2SO4) and evaporated to yield 0.6 g of 3-methoxy-6-nitro-pyridine-2-carbaldehyde as a tan solid. TLC. Rf=0.2 (1.1 ethyl acetate/hexane). 1H NMR (CDCl3) δ 10.1 (s, 1H), 8.5 (d, 1H), 7.85 (d, 1H), 4.15 (s, 3H).

Provenance & Evidence