Hydrochloric Acid → 1-(Imidazo[1,2-a]pyridin-6-yl)propan-2-one

HRID 1381675Notes

Reaction equation

HRID 1381675 reaction equation
[N+]([C:4]([CH3:15])=[CH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[CH:13][N:14]=2)[CH:11]=1)([O-])=O.Cl.[OH2:17]>CCO>[N:14]1[CH:13]=[CH:12][N:10]2[CH:11]=[C:6]([CH2:5][C:4](=[O:17])[CH3:15])[CH:7]=[CH:8][C:9]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 539155686-(2-Nitro-1-propenyl)imidazo[1,2-a]pyridine

Product 1

HCID 138523111-(Imidazo[1,2-a]pyridin-6-yl)propan-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 25 ml of water and 25 ml of EtOH, 1.14 g of 6-(2-nitro-1-propenyl)imidazo[1,2-a]pyridine was heated to 80° C. together with 100 mg of ferrous chloride. With stirring, 2.5 ml of conc. hydrochloric acid was added at a refluxing rate and the mixture was stirred for 1 hour. Upon heating, insoluble matters were removed by filtration. After the insoluble matters were thoroughly washed with ethanol, the solvent was removed by distillation under reduced pressure. An aqueous sodium bicarbonate solution was added to the residue and the mixture was extracted with chloroform. After washing with water and drying over magnesium sulfate, chloroform was removed by distillation under reduced pressure. The residue was purified by column chromatography to obtain 500 mg of 1-(imidazo[1,2-a]pyridin-6-yl)-2-propanone.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. temperatureUpon heating
  3. custominsoluble matters were removed by filtration
  4. washAfter the insoluble matters were thoroughly washed with ethanol
  5. customthe solvent was removed by distillation under reduced pressure
  6. additionAn aqueous sodium bicarbonate solution was added to the residue
  7. extractionthe mixture was extracted with chloroform
  8. washAfter washing with water
  9. dry with materialdrying over magnesium sulfate, chloroform
  10. customwas removed by distillation under reduced pressure
  11. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e45b06a864204339b145987182d02c6b
Source dataset
uspto-grants-1989_02
Patent number
US04803276

Reaction notes

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