Methanol → HCID 66881440, compound

HRID 910080Notes

Reaction equation

HRID 910080 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-947705f414954745aff9ecd4753c5409
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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