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Water → 1-(3-Chloro-5-hydroxypyridin-2-yl)ethanone

HRID 56060
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HRID 56060 반응식
[Cl:1][C:2]1[C:3]([C:9](=[O:11])[CH3:10])=[N:4][CH:5]=[C:6](Cl)[CH:7]=1.C(=O)([O-])[O-:13].[K+].[K+].C(=NO)C.O>CS(C)=O>[Cl:1][C:2]1[C:3]([C:9](=[O:11])[CH3:10])=[N:4][CH:5]=[C:6]([OH:13])[CH:7]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 7863AldoximeHCID 11430Potassium CarbonateHCID 217121631-(3,5-Dichloropyridin-2-yl)ethanone

생성물 1

HCID 666669611-(3-Chloro-5-hydroxypyridin-2-yl)ethanone수율 29.1%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
80 °C

실험 절차

To a solution of 3.8 g of the 1-(3,5-dichloropyridin-2-yl)ethanone prepared in Step 1 in Synthetic Example 2 and 13.8 g of potassium carbonate in 20 ml of dimethylsulfoxide, 5.9 g of acetaldoxime was added, and the mixture was stirred at 80° C. for 4 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, mixed with 50 ml of water and washed with diethyl ether (30 ml×1), the resulting aqueous layer was acidified with 6N aqueous hydrochloric acid and extracted with ethyl acetate (25 ml×2). The resulting organic layers were combined, dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.0 g of desired crude product as brown crystals. The crystals were used in the next step without further purification.

후처리

  1. customAfter completion of the reaction
  2. temperatureto cool to room temperature
  3. washwashed with diethyl ether (30 ml×1)
  4. extractionextracted with ethyl acetate (25 ml×2)
  5. dry with materialdried over saturated aqueous sodium chloride
  6. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-158a104ff5c14a359c477122e58f77c9
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09434684B2

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