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The Royal Society of Chemistry"

N-Oxidation of 5-hydroxy-2-methylpyridine

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Submitted: March 26, 2012, published: March 29, 2012

Authors

A contribution from 

Reaction Scheme

Chemicals

3-Chloroperoxybenzoic acid
5-hydroxy-2-methylpyridine
Chloroform
Ethyl Acetate

Procedure

3-Chloroperoxybenzoic acid (77%, 58.04 g, 259 mmol, 1.1 eq.) was added slowly as a solid to a suspension of 5-hydroxy-2-methylpyridine (25.44 g, 233 mmol) in chloroform (600 ml). After all the solid had dissolved to leave a clear yellow solution, the reaction was stirred at reflux (75°C) for 2 h. After this time the solution was allowed to cool to ambient temperature before the solvent was removed under reduced pressure. The crude yellow solid was washed with hot ethyl acetate (3 × 300 ml) and dried overnight in vacuo. Yield = 22.33 g, 77%.

Author Comments

  • Reaction can be carried out on smaller or larger scale with relative ease
  • Add mCPBA slowly (exothermic reaction)

Data

1H NMR (400 MHz, 298 K, DMSO) δH 10.24 (1H, br s, OH), 7.81 (1H, d, 4JHH = 2.0 Hz, Py), 7.24 (1H, d, 3JHH = 8.5 Hz, Py), 6.77 (1H, dd, 3JHH = 8.5 Hz , 4JHH = 2.0 Hz, Py), 2.22 (3H, s, CH3).

13C{1H} NMR (100 MHz, 298K, DMSO) δC 153.9 (Py), 138.9 (Py), 127.3 (Py), 126.0 (Py), 113.7 (Py), 16.2 (CH3).

MS (ESI) m/z 126.3 [M+H]+, 148.2 [M+Na]+.

IR v cm-1 2215 w, 1622 w, 1570 w, 1529 m, 1459 m, 1422 m, 1386 m, 1309 m, 1275 w, 1226 w, 1663 m, 1117 m, 1001 m, 961 m, 887 m, 863 s, 825 s, 775 m, 740 s, 692 m.

Elemental Analysis found (Calculated for C6H7NO2) % C 57.57 (57.59), H 5.62 (5.64), N 11.05 (11.19).

Lead Reference

M. Seredyuk, A. B. Gaspar, V. Ksenofontov, Y. Galyametdinov, J. Kusz and P. Gütlich, J. Am. Chem. Soc., 2008, 130, 1431-1439

Keywords

heterocyclic compounds, N-Oxidation, oxidation