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Dimethylformamide → 1-(4-Methoxyphenyl)pyridin-2(1H)-one

HRID 1693079
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HRID 1693079 반응식
[C:1](=[O:4])([O-])[O-].[K+].[K+].CN(C)C=O.O[C:13]1[CH:18]=C[N:16]=[CH:15][CH:14]=1.I[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1>[Cu](I)I.O>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([N:16]2[CH:15]=[CH:14][CH:13]=[CH:18][C:1]2=[O:4])=[CH:21][CH:22]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 696764-IodoanisoleHCID 178418642HCID 178418642, 화합물

생성물 1

HCID 121913851-(4-Methoxyphenyl)pyridin-2(1H)-one수율 51.4%

시약·촉매·용매 2

HCID 83717Copper iodide촉매
HCID 962
Water
용매

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온도
150 °C

실험 절차

Potassium carbonate (1.16 g, 8.41 mmol) and copper iodide (16 mg, 0.084 mmol) were added to a dimethylformamide (12 mL) solution of 4-hydroxypyridine (800 mg, 8.41 mmol) and 4-iodo-1-methoxybenzene (3.94 g, 16.8 mmol), and stirred at 150° C. for 21 hours. The reaction mixture was cooled to room temperature, then water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried with anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, hexane/ethyl acetate=1/1) to obtain the entitled compound (870 mg, 51%).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (C-300, hexane/ethyl acetate=1/1)

출처 및 근거

ORD 기록
ord-369dc2aa1d444e1799749a86758b7447
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08158652B2

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