Chloroacetone → HCID 58629107, compound

HRID 1678063Notes

Reaction equation

HRID 1678063 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].[CH3:6][O:7][C:8]1[N:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].[K+]>[CH3:6][O:7][C:8]1[N:13]=[CH:12][C:11]([O:14][CH2:2][C:3]([CH3:4])=[O:5])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 6571Chloroacetone2×HCID 11430Potassium Carbonate2×HCID 116223355-Hydroxy-2-methoxypyridine

Product 1

HCID 58629107HCID 58629107, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of chloroacetone (3.7 g) and potassium iodide (65 mg) in acetone (7 mL) was stirred at approximately 25° C. overnight. In a second reactor, 6-methoxypyridin-3-ol (4.0 g, mmol) and potassium carbonate (1.3 g, 10 mmol) in acetone (5 mL) was refluxed for 15 min., then ¼ of chloroacetone/KI solution was added followed by additional potassium carbonate (1.3 g). This was repeated three times more, then the reaction stirred at approximately 25° C. overnight. The mixture was concentrated in vacuo. The residue was dissolved in Et2O and washed with H2O, brine and dried with Na2SO4. The solution was filtered and concentrated in vacuo yielding 3.5 g of clear oil that was used without further purification. This material darkened on standing over time.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in Et2O
  3. washwashed with H2O, brine
  4. dry with materialdried with Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b160fc6b86b48cdb6c820a307c7581c
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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