Acetic Anhydride → HCID 23134654, compound

Participants

Reaction Conditions

Reaction Steps

4-Iodo-2-methylaniline (30.2 g, 130 mmol) was dissolved in chloroform (300 mL) and cooled to 5° C. Acetic anhydride (35 mL, 343 mmol) was added dropwise, and the mixture was allowed to warm to ambient temperature. Potassium acetate (4.21 g, 42.9 mmol) and isoamylnitrite (37 mL, 277 mmol) were added, and the mixture was heated to 70° C. overnight. The mixture was neutralized with saturated aqueous sodium bicarbonate and extracted with methylene chloride. The solvents were removed under reduced pressure and the resulting residue was triturated with methanol to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.41 (s, 1H) 8.33 (s, 1H) 8.05-8.21 (m, 1H) 7.90 (dd, J=8.48, 1.70 Hz, 1H) 2.71 (s, 3H).

Provenance & Evidence