Water → HCID 18182460, compound

HRID 1359315Notes

Reaction equation

HRID 1359315 reaction equation
[CH2:1]([C:8]1[C:9]([O:17][CH3:18])=[N:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[CH2:1]([C:8]1[C:9]([O:17][CH3:18])=[N:10][CH:11]=[C:12]([C:14]([O:16][CH3:19])=[O:15])[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18182316HCID 18182316, compound

Product 1

HCID 18182460HCID 18182460, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.1 g of 3-benzyl-2-methoxypyridine-5-carboxylic acid and 2.9 g of potassium carbonate was suspended in 40 ml of N,N-dimethylformamide. 1.1 ml of methyl iodide was added-thereto at room temperature under stirring. After stirring for 40 minutes, water was added thereto and extracted with ethyl acetate. The organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvent was evaporated. The residue was subjected to silica gel column chromatography using 11-14% ethyl acetate/hexane as an eluent for separation and purification, to give 2.2 g of the target compound.

Workup

  1. stirringAfter stirring for 40 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was further washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customfor separation and purification

Sources & evidence

ORD record
ord-e504c3474e3b4fcea3f8de6cb5f3a7cf
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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