Methanol → HCID 66881440, compound

HRID 557179Notes

Reaction equation

HRID 557179 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[N:7]1[CH:8]=[CH:9][N:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=12.[CH3:16][OH:17]>C1(C)C=CC=CC=1>[CH3:16][O:17][C:1](=[O:5])[C:2]([C:9]1[N:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]2=[N:7][CH:8]=1)=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 78960Imidazo(1,2-a)pyridine

Product 1

HCID 66881440HCID 66881440, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add oxalyl chloride (2.13 g, 1.46 ml, 16.8 mmol) to a solution of imidazo[1,2-a]pyridine (1.0 g, 8.47 mmol) in toluene (75 ml). Heat the mixture at reflux for 15 hours. Cool the reaction and gently add methanol. Concentrate the resulting mixture under reduced pressure and partition between hot ethyl acetate and saturated aqueous sodium bicarbonate. Wash organic phase with saturated aqueous sodium chloride, dry over magnesium sulfate, and concentrate under reduced pressure. Triturate in ethyl acetate to give the title compound as an off-white solid (0.75 gm).

Workup

  1. temperatureHeat the mixture
  2. temperatureat reflux for 15 hours
  3. temperatureCool
  4. concentrationConcentrate the resulting mixture under reduced pressure
  5. custompartition between hot ethyl acetate and saturated aqueous sodium bicarbonate
  6. dry with materialWash organic phase with saturated aqueous sodium chloride, dry over magnesium sulfate
  7. concentrationconcentrate under reduced pressure
  8. customTriturate in ethyl acetate

Sources & evidence

ORD record
ord-d942aab1ad9c420b98ec51afdecff6ed
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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