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

HRID 968715노트

반응식

HRID 968715 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-53b672d15bc4434c9dbc2f5a36f76eb0
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07304074B2

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