Iodine → HCID 12399250, compound

HRID 1284094Notes

Reaction equation

HRID 1284094 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)(=O)[CH3:2].II.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>C(O)C>[N:18]1[C:1]([C:4]2[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=2)=[CH:2][N:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=12

Participants

5

Reactant 3

HCID 807IodineHCID 104392-AminopyridineHCID 73716Ethyl (4-acetylphenyl)acetate

Product 1

HCID 12399250HCID 12399250, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6 g of ethyl 4-acetylphenylacetate, 20 ml of ethanol, 7.5 g of iodine and 5.7 g of 2-aminopyridine is heated under reflux for 3 hours. The ethanol is distilled off under reduced pressure, and the residue is extracted with ethyl acetate. The extract is washed with water, dried, and concentrated to give a reddish brown oil. The oil is column chromatographed over silica gel with chloroform as eluent, and the colorless crystals obtained from the chloroform eluate are recrystallized from a mixture of benzene and petroleum ether to give 3.0 g of ethyl 4-(imidazo[1,2-a]pyridin-2-yl)phenylacetate melting at 92°-93°C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. distillationThe ethanol is distilled off under reduced pressure
  4. extractionthe residue is extracted with ethyl acetate
  5. washThe extract is washed with water
  6. customdried
  7. concentrationconcentrated
  8. customto give a reddish brown oil
  9. customchromatographed over silica gel with chloroform as eluent
  10. customthe colorless crystals obtained from the chloroform eluate
  11. customare recrystallized from a mixture of benzene and petroleum ether

Sources & evidence

ORD record
ord-e0166e7686ef44b18b89aaec796842ea
Source dataset
uspto-grants-1976_08
Patent number
US03978071

Reaction notes

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