1,4-Dioxane → 6-Formyl-[1,5]naphthyridine-3-carbonitrile

HRID 968726Notes

Reaction equation

HRID 968726 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[CH:5]2.[O:14]1CCOCC1>>[CH:1]([C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[CH:5]2)=[O:14]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 587243266-Methyl-[1,5]naphthyridine-3-carbonitrile

Product 1

HCID 587243016-Formyl-[1,5]naphthyridine-3-carbonitrileYield 100%

Procedure

To a solution of 6-methyl-[1,5]naphthyridine-3-carbonitrile (220.0 mg, 1.30 mmol) in 1,4-dioxane was added SeO2 (187.6 mg, 1.70 mmol) and the reaction mixture was refluxed for 2 hrs, when the TLC showed no starting material left, then cooled to room temperature and filtered through celite. The solid was washed with hot AcOEt and the filtrate was then concentrated to give 6-formyl-[1,5]naphthyridine-3-carbonitrile as a light yellow solid (238.1 mg, 100.0%). HR-MS-EI (+) m/e calcd for C10H5N3O (M+) 183.0433. found 183.0433

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hrs
  2. waitleft
  3. filtrationfiltered through celite
  4. washThe solid was washed with hot AcOEt
  5. concentrationthe filtrate was then concentrated

Sources & evidence

ORD record
ord-ddf90a9a64934f7dad92596ee00dd07f
Source dataset
uspto-grants-2007_12
Patent number
US07304074B2

Reaction notes

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