Methyl iodide → 1,3-Dihydro-5-methoxy-1-methyl-2H-indol-2-one

Participants

Reaction Steps

5-methoxy oxindole (450 mg, 2.76 mmol) and potassium carbonate (585 mg, 4.23 mmol) were combined in 45 ml of acetone under an inert atmosphere. To this white, heterogenous mixture was added 0.33 ml of methyl iodide (5.30 mmol) via syringe. The reaction mixture was stirred at room temperature for 10 hours and then at 75° C. for 3 hours. Additional potassium carbonate and methyl iodide were added (290 mg and 0.11 ml, respectively), and the reaction mixture was stirred at 75° C. for 6 more hours. The reaction mixture was then poured into 300 ml of saturated brine solution and extracted with 3×200 ml ether. The combined organic layers were dried over MgSO4, filtered, and stripped to a yellow oil. This was purified via flash chromatography (3:1 ethyl ether/hexane) to provide the title compound (307 mg, 63% yield) as white crystals: m.p. 93°-94° C. M/z calculated for C10H11NO2 : 177.0790, Found: 177.08066.

Provenance & Evidence