Ethanol → HCID 12399250, compound

HRID 1284087Notes

Reaction equation

HRID 1284087 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1)=O.C(O)C.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1>CCOCC>[N:20]1[C:3]([C:5]2[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=2)=[CH:2][N:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=12

Participants

5

Reactant 3

HCID 702EthanolHCID 104392-AminopyridineHCID 12399236HCID 12399236, compound

Product 1

HCID 12399250HCID 12399250, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 96 g of ethyl 4-(chloroacetyl)phenylacetate, 200 ml of ethanol and 64 g of 2-aminopyridine is heated under reflux for 2 hours. The ethanol is distilled off under reduced pressure, and water is added to the residue. The mixture is extracted with benzene, and the extract is washed with water, dried and concentrated to give a brown oil. To the oil is added ether, and the crystalline precipitate is filtered off and recrystallized from a mixture of benzene and petroleum ether to give 44 g of ethyl 4-(imidazo[1,2-a]pyridin-2-yl)phenylacetate as pale brown crystals melting at 92°-93°C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. distillationThe ethanol is distilled off under reduced pressure, and water
  4. additionis added to the residue
  5. extractionThe mixture is extracted with benzene
  6. washthe extract is washed with water
  7. customdried
  8. concentrationconcentrated
  9. customto give a brown oil
  10. filtrationthe crystalline precipitate is filtered off
  11. customrecrystallized from a mixture of benzene and petroleum ether

Sources & evidence

ORD record
ord-3b1ab6daee694e8c9cfe81bfd4f2d7db
Source dataset
uspto-grants-1976_08
Patent number
US03978071

Reaction notes

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