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Oxindole (2.00 g, 0.0150 mol), 1-bromo-3-chloropropane (2.97 mL, 0.03 mol), and potassium carbonate (4.15 g, 0.03 mol) in acetonitrile (40 mL) were heated at reflux for 20 hours. The mixture was evaporated, diluted with ethyl acetate, washed with 2M aqueous hydrochloric acid and brine, dried (MgSO4), and evaporated. The residue was purified by Biotage flash column chromatography (30% ethyl acetate/hexanes) to give product as an oil which solidified on standing (1.57 g, 50%); MS for C11H12ClNO m/z 210 (M+H)+.

1. temperatureat reflux for 20 hours
2. customThe mixture was evaporated
3. additiondiluted with ethyl acetate
4. washwashed with 2M aqueous hydrochloric acid and brine
5. dry with materialdried (MgSO4)
6. customevaporated
7. customThe residue was purified by Biotage flash column chromatography (30% ethyl acetate/hexanes)
8. customto give product as an oil which