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Aniline (9.11 mL, 100 mmol) was dissolved in acetonitrile (100 mL) and heated to reflux while β-propiolactone (Sigma, 6.29 mL, 100 mmol) in acetonitrile (20 mL) was added dropwise for 30 minutes. The mixture was refluxed for 3 hours and then stirred overnight at ambient temperature. The mixture was concentrate under reduced pressure, and chromatographed on silica gel eluting with 40-to-100% ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 2.69 (t, J=6.27 Hz, 2H), 3.48 (t, J=6.44 Hz, 2H), 6.66 (dd, J=8.81, 1.02 Hz, 2H), 6.75 (t, J=7.46 Hz, 1H), 7.20 (dd, J=8.65, 7.29 Hz, 2H). MS (DCI) m/z 166.05 (M+H)+.

1. temperatureheated
2. additionwas added dropwise for 30 minutes
3. temperatureThe mixture was refluxed for 3 hours
4. concentrationThe mixture was concentrate under reduced pressure
5. customchromatographed on silica gel eluting with 40-to-100% ethyl acetate in hexane