Acetic Anhydride → HCID 57585973, compound

Participants

Reaction Steps

4-{[4-(1,3-dioxolan-2-yl)phenyl]oxy}-2-methylaniline (1.24 g, 4.55 mmol) in 40 mL tetrahydrofuran at room temperature was treated with potassium acetate (490 mg, 5 mmol) followed by acetic anhydride (1.42 mL, 15 mmol). After 10 minutes, the reaction was treated with isoamylnitrite (0.915 mL, 6.8 mmol) and heated to reflux for 3 hours. Catalytic 18-crown-6 was added and the reaction was refluxed for 4 days. Upon cooling to room temperature, the reaction mixture was poured into saturated aqueous NaHCO3 and extracted with ethylacetate. The organic was rinsed with brine, dried over MgSO4, and concentrated. The crude material was purified via silica gel column chromatography (0% to 100% ethyl acetate in hexane gradient) to provide 0.835 g 1-acetyl-5-{[4-(1,3-dioxolan-2-yl)phenyl]oxy}-1H-indazole.

Provenance & Evidence