Chloroacetone → HCID 54100482, compound

HRID 2399164Notes

Reaction equation

HRID 2399164 reaction equation
[OH:1][C:2]1[C:3]([C:8]([NH2:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C:19](=[O:21])[CH3:20]>C(#N)C>[O:21]=[C:19]([CH3:20])[CH2:18][O:1][C:2]1[C:3]([C:8]([NH2:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 702773-Hydroxypicolinamide

Product 1

HCID 54100482HCID 54100482, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 27.6 g of 3-hydroxy-2-pyridinecarboxylic acid amide and 31 g of potassium carbonate in 600 ml of acetonitrile is heated to the boil for 2 hours, while stirring well. 22.2 g of chloroacetone are added dropwise to the resulting thick paste in the course of 30 minutes. The reaction mixture is stirred for 20 hours whilst boiling under reflux. The undissolved material is filtered off after cooling and the filtrate is evaporated under reduced pressure. The residue is stirred with water, whereupon unconverted 3-hydroxy-2-pyridinecarboxylic acid amide remains as an undissolved residue. The aqueous solution is evaporated under reduced pressure and the residue is extracted with methylene chloride. The organic solution, after evaporation under reduced pressure, gives crude 3-(2-oxo-propoxy)-2-pyridinecarboxylic acid amide which melts at 135°-140° C. after crystallisation from ethanol.

Workup

  1. temperatureis heated to the boil for 2 hours
  2. stirringThe reaction mixture is stirred for 20 hours
  3. temperatureunder reflux
  4. filtrationThe undissolved material is filtered off
  5. temperatureafter cooling
  6. customthe filtrate is evaporated under reduced pressure
  7. stirringThe residue is stirred with water, whereupon unconverted 3-hydroxy-2-pyridinecarboxylic acid amide
  8. customThe aqueous solution is evaporated under reduced pressure
  9. extractionthe residue is extracted with methylene chloride
  10. customThe organic solution, after evaporation under reduced pressure

Sources & evidence

ORD record
ord-fbd942c4cb994346a6c6ffd27d23e7c3
Source dataset
uspto-grants-1977_05
Patent number
US04027027

Reaction notes

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