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

HRID 916244Notes

Reaction equation

HRID 916244 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

To a solution of 2-methyl-1,5-naphthyridine (216.0 mg, 1.5 mmol) in 1,4-dioxane (5 mL) was added SeO2 (183.0 mg, 1.65 mmol) and the reaction mixture was refluxed for 0.5 hr, when the TLC showed no starting material left, then cooled to room temperature and filtered through celite. The solvent was removed under reduced pressure and the residue was purified by Biotage column (AcOEt: nHex=3:1) to give [1,5]naphthyridine-2-carbaldehyde as a white solid (142.3 mg, 60.0). LR-ES m/e 159 (MH+).

Workup

  1. temperaturethe reaction mixture was refluxed for 0.5 hr
  2. waitleft
  3. filtrationfiltered through celite
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by Biotage column (AcOEt: nHex=3:1)

Sources & evidence

ORD record
ord-0d51c15375be475ea4b075a187389d73
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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