6-(Hydroxymethyl)pyridin-3-ol (6.74 g, 53.86 mmol, 1.0 eq.) was dissolved in isopropanol (200 ml) to give a brown solution. Activated manganese(IV) oxide (11.71 g, 86.94 mmol, 2.5 eq.) was then added as a solid. The black mixture was stirred at reflux (100°C) for 4 h and then stirred at ambient temperature for a further 18 h. The solution was filtered through celite and the remaining MnO₂ was washed with isopropanol (5 × 150 ml). The solvent was removed from the filtrate under reduced pressure to leave a yellow-brown solid. The solid was recrystallised from hot water (~ 20 ml) to leave the pure product as brown crystals. Yield = 3.99 g, 32.41 mmol, 60%.

¹H NMR (400 MHz, 298 K, DMSO) δ_H 11.11 (1H, br s, OH), 9.83 (1H, s, HC=O), 8.31 (1H, d, ⁴J_HH = 2.5 Hz, Py), 7.84 (1H, d, ³J_HH = 8.5 Hz, Py), 7.33 (1H, dd, ³J_HH = 8.5 Hz, ⁴J_HH = 2.5 Hz, Py).

¹³C{¹H} NMR (100 MHz, 298K, DMSO) δ_C 191.8 (C=O), 157.9 (Py), 144.7 (Py), 138.7 (Py), 123.6 (Py), 122.3 (Py).

MS (ESI) m/z 124.3 [M+H]⁺, 146.2 [M+Na]⁺, 122.0 [M-H]^-.

IR v cm^-1 2506 w, 1694 m, 1597 w, 1567 s, 1471 w, 1311 m, 1273 m, 1209 s, 1115 s, 1024 m, 911 m, 871 m, 847 s, 790 s, 730 m, 660 s.

Elemental Analysis found (Calculated for C₆H₅NO₂) % C 58.47 (58.54), H 4.07 (4.09), N 11.22 (11.38).