Hydrochloric Acid → 5-Fluoro-3,4-dihydroquinolin-2(1H)-one

Temperature

90 °C

To a stirred solution of diethyl 2-(2-amino-6-fluorobenzyl)malonate (146-3; 2.0 g, 0.00706 mol)) in acetic acid (20 mL) was added hydrochloric acid (20 mL). The reaction mixture was heated at 90° C. for 1 h. The reaction mixture was cooled to room temperature and then poured into ice cold water. It was extracted with ethyl acetate (3×40 mL). The combined organic layer was washed with 10% aqueous sodium hydroxide solution, saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to afford the title compound. 1H NMR (400 MHz, DMSO) δ 10.219 (s, 1H), 7.164-7.108 (q, J=7.6 Hz, 1H), 6.769-6.725 (t, J=8.4 Hz, 1H), 6.684-6.664 (d, J=8.0 Hz, 1H), 2.871-2.832 (t, J=7.6 Hz, 2H), 2.472-2.434 (t, J=8.0 Hz, 2H). MS (M+1): 166.1.

1. temperatureThe reaction mixture was cooled to room temperature
2. additionpoured into ice cold water
3. extractionIt was extracted with ethyl acetate (3×40 mL)
4. washThe combined organic layer was washed with 10% aqueous sodium hydroxide solution, saturated aqueous sodium chloride solution
5. dry with materialdried over sodium sulphate
6. concentrationconcentrated under vacuum

ORD record

ord-2463368a440045f193bbc6e6630ccf1b

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073929B2