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

HRID 968715Notes

Reaction equation

HRID 968715 reaction equation
[CH:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH3:15])[N:13]=2)[N:8]=[CH:7][C:6]=1[C:16]#[N:17])([CH3:3])[CH3:2].[O:18]1CCOCC1>>[CH:15]([C:12]1[N:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:16]#[N:17])=[C:5]2[O:4][CH:1]([CH3:3])[CH3:2])=[O:18]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 587243144-Isopropoxy-6-methyl-[1,5]naphthyridine-3-carbonitrile

Product 1

HCID 587243116-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile

Procedure

To a solution of 4-isopropoxy-6-methyl-[1,5]naphthyridine-3-carbonitrile (260.0 mg, 1.14 mmol) in 1,4-dioxane was added SeO2 (165.0 mg, 1.48 mmol) and the reaction mixture was refluxed for 3.5 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-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile as a light yellow solid (270.3 mg, 98.3). HR-MS-EI (+) m/e calcd for C13H11N3O2 (M+) 241.0851. found 241.0854.

Workup

  1. temperaturethe reaction mixture was refluxed for 3.5 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-53b672d15bc4434c9dbc2f5a36f76eb0
Source dataset
uspto-grants-2007_12
Patent number
US07304074B2

Reaction notes

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