Acetic Anhydride → 4-ethoxy-1H-pyridin-2-one

Temperature

25 °C

A mixture of 4-ethoxypyridine 1-oxide (5 g, 35.9 mmol) in acetic anhydride (36.7 g, 359 mmol) was heated to reflux for 4 h. Then the solvent was removed in vacuo, and the residue was dissolved in MeOH (25 mL) and H2O (25 mL) and stirred at 25° C. for 16 h. The mixture was concentrated. The crude material was purified by silica column chromatography (DCM/MeOH=10:1). All fractions found to contain product by TLC (DCM/MeOH=10:1, Rf=0.6) were combined and concentrated to yield a dark yellow solid of 4-ethoxypyridin-2-ol (2.5 g, 16.17 mmol, 45.0% yield): 1H NMR (400 MHz, CD3OD) δ 7.28 (d, J=7.6 Hz, 1H), 6.07 (d, J=3.2, 7.2 Hz, 1H), 5.86-7.85 (d, J=2.4 Hz, 1H), 4.06-4.01 (m, 2H), 1.38 (t, J=7.2 Hz, 3H); ES-LCMS m/z 140.0 (M+H).

1. temperaturewas heated
2. temperatureto reflux for 4 h
3. customThen the solvent was removed in vacuo
4. dissolutionthe residue was dissolved in MeOH (25 mL)
5. concentrationThe mixture was concentrated
6. customThe crude material was purified by silica column chromatography (DCM/MeOH=10:1)
7. concentrationconcentrated

ORD record

ord-2bff313415e74ec18d9e8ddaf6503d7b

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382238B2