Phenol → HCID 59442723, compound

Participants

Reaction Steps

To a solution of 2-amino-4-nitrophenol 28 (15 g, 97.32 mmol, 1 equiv) in dimethylformamide (300 mL) under nitrogen gas, was added potassium carbonate (40.35 g, 292 mmol, 3 equiv) and isopropyl iodide (9.73 mL, 16.54 g, 97.32 mmol, 1 equiv), then the reaction mixture was stirred at ambient temperature overnight. LCMS analysis of the reaction mixture indicated a mixture of starting material:phenol alkylation: aniline phenol dialkylation (20:13:67). The reaction mixture was diluted with ethyl acetate and water. The layers were separated, and the organic layer was washed with water 1×, dried over Na2SO4, filtered, and concentrated. The crude reaction mixture was purified by flash chromatography and eluted with dichloromethane to provide 2-isopropoxy-N-isopropyl-5-nitrobenzenamine 29 (2.42 g, 10%) as an oil.

Provenance & Evidence