Water → HCID 58047520, compound

HRID 1888727Notes

Reaction equation

HRID 1888727 reaction equation
[OH:1][C:2]1[C:3]([CH:9]=O)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].O>CN(C=O)C>[CH3:8][C:5]1[N:4]=[C:3]2[CH:9]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[O:1][C:2]2=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 124219863-Hydroxy-6-methylpyridine-2-carbaldehyde

Product 1

HCID 58047520HCID 58047520, compoundYield 233.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-hydroxy-6-methylpyridine-2-carbaldehyde (4.92 mmol, 35.9 mmol) in DMF (70 mL) were added potassium carbonate (9.93 g, 71.8 mmol) and ethyl bromoacetate (5.97 mL, 53.9 mmol), and the mixture was stirred at 100° C. for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 3:2) to give the title compound (2.36 g, yield 32%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 3:2)

Sources & evidence

ORD record
ord-7274001fdc504019a5da22138f8d84c8
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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