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

HRID 56060
Notes
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Reaction equation

HRID 56060 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-158a104ff5c14a359c477122e58f77c9
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434684B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes