HCID 72297485, compound → HCID 59432593, compound

Participants

Reaction Steps

Heat a mixture of 2,3-dimethoxy-5-nitro-6-(2-nitrovinyl)pyridine, 8 (144 mg, 0.565 nmmol), Fe (0.6 g, 0.565 nmmol), SiO2 (0.565 g) under reflux in ACOH (3.4 mL) and toluene (5.7 mL). After 1 h, leave the reaction medium to cool to room temperature. Filter the reaction mixture and wash the solid with CH2Cl2 and discard. Then wash the filtrate with aqueous Na2SO3 at 1%/Na2S2O5, then with saturated NaHCO3, dry (MgSO4) and concentrate under vacuum. Purify the raw product by flash chromatography (EtOAc at 40%/heptane) to give 9 (46 mg, 46%) as a fawn-colored solid: 1H NMR (CDCl3) δ 8.04 (s broad, 1H), 7.19 (m, 1H), 7.12 (s, 1H), 6.55 (m, 1H), 4.09 (s, 3H), 3.90 (s, 3H); Rf (EtOAc at 40%/heptane)=0.10; m/z obs.=178.94 (M+1).

Provenance & Evidence