Selenium Dioxide → 2-PYRIDINECARBOXALDEHYDE, 1-OXIDE

HRID 983633Notes

Reaction equation

HRID 983633 reaction equation
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

Participants

4

Reactant 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 12010033-Bromo-2-methylpyridine

Product 1

HCID 5560312-PYRIDINECARBOXALDEHYDE, 1-OXIDEYield 29%

Procedure

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).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by column chromatography on silica gel (Hexanes/ether, 3:1)

Sources & evidence

ORD record
ord-6d8819c6e93943bdbecb86bab71e0b03
Source dataset
uspto-grants-2005_03
Patent number
US06864265B2

Reaction notes

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