Potassium Carbonate → 1-(2-hydroxyethyl)-4-iodopyridin-2(1H)-one

HRID 470431Notes

Reaction equation

HRID 470431 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.I[CH2:10][CH2:11][OH:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:12][CH2:11][CH2:10][N:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][C:4]1=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12225IodoethanolHCID 205825354-Iodo-1,2-dihydropyridin-2-one

Product 1

HCID 596357681-(2-hydroxyethyl)-4-iodopyridin-2(1H)-oneYield 106.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the mixture of 4-iodopyridin-2(1H)-one (50 mg, 0.213 mmol) in DMF (3 mL) was added 2-iodoethanol (73 mg, 0.426 mmol), K2CO3 (88 mg, 0.638 mmol) at rt. The mixture was stirred for 2 h at rt. After the reaction was finished, the mixture was washed with water and extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated to give the crude product, which was purified by TLC to provide 1-(2-hydroxyethyl)-4-iodopyridin-2(1H)-one (60 mg 100%).

Workup

  1. washthe mixture was washed with water
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas purified by TLC

Sources & evidence

ORD record
ord-858fa1974a7e43b38cc3f24d2cf103db
Source dataset
uspto-grants-2014_01
Patent number
US08629138B2

Reaction notes

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