Ethanol → ethyl 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxylate

HRID 1392119Notes

Reaction equation

HRID 1392119 reaction equation
Cl[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][N:10]=1.[CH2:16](O)[CH3:17]>>[CH2:6]([O:5][C:3]([C:2]1[N:10]2[CH:11]=[CH:12][C:13]([CH3:15])=[CH:14][C:9]2=[N:8][C:16]=1[CH3:17])=[O:4])[CH3:7]

Participants

4

Reactant 3

HCID 702EthanolHCID 15332-Amino-4-methylpyridineHCID 7751Ethyl chloroacetate

Product 1

HCID 682232ethyl 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxylateYield 35%

Procedure

15.2 g ethyl 2-chloroacetate were added to a solution of 10 g 2-amino-4-methylpyridine in 200 ml ethanol, the mixture was stirred under reflux for 8 hours and the reaction solution was stirred overnight at room temperature. After removal of the solvent, the residue was taken up with aqueous 10% strength HCl, and the mixture was washed with methylene chloride, rendered basic with sodium bicarbonate and extracted with methylene chloride. The combined organic phases were washed with water and dried over sodium sulfate. After removal of the solvent and purification by column chromatography, the product was obtained in a yield of 35%.

Workup

  1. temperatureunder reflux for 8 hours
  2. stirringthe reaction solution was stirred overnight at room temperature
  3. customAfter removal of the solvent
  4. washthe mixture was washed with methylene chloride
  5. extractionextracted with methylene chloride
  6. washThe combined organic phases were washed with water
  7. dry with materialdried over sodium sulfate
  8. customAfter removal of the solvent and purification by column chromatography
  9. customthe product was obtained in a yield of 35%

Sources & evidence

ORD record
ord-82487881fb8f41589728056dbb69901e
Source dataset
uspto-grants-2008_03
Patent number
US07342025B2

Reaction notes

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