1,4-Dioxane → 1,5-Naphthyridine-2-carbaldehyde

HRID 1890587Notes

Reaction equation

HRID 1890587 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[N:3]=1.[O:12]1CCOCC1>>[N:3]1[C:4]2[C:9](=[N:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[CH:1]=[O:12]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 5890332-Methyl-1,5-naphthyridine

Product 1

HCID 115863361,5-Naphthyridine-2-carbaldehyde

Procedure

A mixture of 2-methyl-1,5-naphthyridine (8-2) (2.9 g, 20.1 mmol) and SeO2 (2.2 g, 20.1 mmol) in 40 mL of dioxane was refluxed for 3 h. After cooled to room temperature, the reaction mixture was concentrated. The residue was treated with brine and extracted with DCM/i-PrOH=4/1. The organic layer was washed with brine, dried over Na2SO4, concentrated and purified by chromatography on silica gel to afford the title compound (1.81 g).

Workup

  1. temperaturewas refluxed for 3 h
  2. concentrationthe reaction mixture was concentrated
  3. additionThe residue was treated with brine
  4. extractionextracted with DCM/i-PrOH=4/1
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-6dde9f7f74c04abb97ecb02506fbd8c9
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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