Nitric Acid → HCID 18470694, compound

Participants

Reaction Steps

To a cooled (−10˜−20° C.) acetic anhydride (1.2 mL) was added fuming nitric acid (0.13 mL) and sulfuric acid (1 drop). After stirring for 3 minutes, 3-acetyl-4-methyl-5-(4-pyridyl)-1H-pyrrole (0.2 g, 1 mmol) was added to the mixture. The resulting mixture was allowed to warm to room temperature and stirred for additional 1 hour. The mixture was poured into saturated aqueous NaHCO3. The whole was extracted with ethyl acetate (30 mL×4), the combined organic layers washed with brine, dried over MgSO4, and concentrated in vacito. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (2:1) to provide the title compound (35 mg, 14% yield).

Provenance & Evidence