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

HRID 968726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968726
[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]

Komponenten

3

Edukt 2

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

Produkt 1

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

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ddf90a9a64934f7dad92596ee00dd07f
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304074B2

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