1,4-Dioxane → 8-Isopropoxy-[1,5]naphthyridine-2-carbaldehyde

HRID 968740Notes

Reaction equation

HRID 968740 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[CH:7][N:8]=[C:9]2[C:14]=1[N:13]=[C:12]([CH3:15])[CH:11]=[CH:10]2)([CH3:3])[CH3:2].[O:16]1CCOCC1>>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][N:8]=[C:9]2[C:14]=1[N:13]=[C:12]([CH:15]=[O:16])[CH:11]=[CH:10]2)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 587243298-Isopropoxy-2-methyl-[1,5]naphthyridine

Product 1

HCID 587243028-Isopropoxy-[1,5]naphthyridine-2-carbaldehydeYield 100%

Procedure

To a solution of 8-isopropoxy-2-methyl-[1,5]naphthyridine (1.13 g, 5.60 mmol) in 1,4-dioxane (40 mL) was added SeO2 (0.80 g, 7.20 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 8-isopropoxy-[1,5]naphthyridine-2-carbaldehyde as a light yellow solid (1.20 g, 100%). HR-MS-EI (+) m/e calcd for C12H12N2O2 (M+) 216.0899. found 216.0900

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-5462c74e8a764e8db57793f292003792
Source dataset
uspto-grants-2007_12
Patent number
US07304074B2

Reaction notes

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