Selenium Dioxide → 2-pyridinecarboxaldehyde N-oxide

反応式

Br[C:2]1C(C)=[N:4][CH:5]=[CH:6][CH:7]=1.[Se](=O)=[O:10].[O:12]1[CH2:17][CH2:16]OCC1>>[N+:4]1([O-:10])[C:16]([CH:17]=[O:12])=[CH:2][CH:7]=[CH:6][CH:5]=1

参加物

反応物 3

HCID 24007Selenium Dioxide

HCID 312751,4-Dioxane

HCID 12010033-Bromo-2-methylpyridine

生成物 1

HCID 5560312-pyridinecarboxaldehyde N-oxide収率 29%

実験手順

To a solution of 3-bromo-2-picoline (prepared as described by Guthikonda, R. N.; Cama, L. D.; Quesada, M.; Woods, M. F.; Salzmann, T. N.; Christensen, B. G. J. Med. Chem. 1987, 30, 871-880) (249 mg, 1.45 mmol) in dioxane (2 mL) was added selenium(IV) oxide (212 mg, 1.91 mmol) and the mixture stirred at reflux overnight. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (Hexanes/ether, 3:1) to afford the title compound (78 mg, 29%) as a pale yellow solid. 1H NMR (CDCl3): δ7.38 (dd, 1H, J=9, 6 Hz), 8.05 (d, 1H, J=9 Hz), 8.76 (d, 1H, J=3 Hz), 10.25 (s, 1H).