Diisopropyl Ether → HCID 12399251, compound

HRID 1284088Notes

Reaction equation

HRID 1284088 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1)=O.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C(OC(C)C)(C)C>C(O)C>[N:18]1[C:3]([C:5]2[CH:10]=[CH:9][C:8]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=2)=[CH:2][N:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=12

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 104392-AminopyridineHCID 12399237HCID 12399237, compound

Product 1

HCID 12399251HCID 12399251, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 47 g of ethyl 2-[4-(chloroacetyl)phenyl]propionate, 100 ml of ethanol and 30 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 reddish brown oil. To the oil is added isopropyl ether, and the crystalline precipitate is filtered off and recrystallized from isopropyl ether to give 22 g of ethyl 2-[4-(imidazo[1,2-a]pyridin-2-yl)phenyl]propionate as colorless scales melting at 110°-112°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 reddish brown oil
  10. filtrationthe crystalline precipitate is filtered off
  11. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-bf7f957439414821b045d0afc96667f6
Source dataset
uspto-grants-1976_08
Patent number
US03978071

Reaction notes

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