Methanol → 5-(Imidazo[1,2-a]pyridin-6-yl)-2-methoxy-6-methyl-3-pyridinecarbonitrile

HRID 579963Notes

Reaction equation

HRID 579963 reaction equation
C(Cl)Cl.Cl[C:5]1[C:10]([C:11]#[N:12])=[CH:9][C:8]([C:13]2[CH:14]=[CH:15][C:16]3[N:17]([CH:19]=[CH:20][N:21]=3)[CH:18]=2)=[C:7]([CH3:22])[N:6]=1.[CH3:23][OH:24]>>[N:21]1[CH:20]=[CH:19][N:17]2[CH:18]=[C:13]([C:8]3[CH:9]=[C:10]([C:11]#[N:12])[C:5]([O:24][CH3:23])=[N:6][C:7]=3[CH3:22])[CH:14]=[CH:15][C:16]=12

Participants

4

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 138523142-Chloro-5-(imidazo[1,2-a]pyridin-6-yl)-6-methylpyridine-3-carbonitrile

Product 1

HCID 138523345-(Imidazo[1,2-a]pyridin-6-yl)-2-methoxy-6-methyl-3-pyridinecarbonitrile

Procedure

In a solvent mixture of 30 ml of methylene chloride and 30 ml of methanol, 0.59 g of 2-chloro-5-(imidazo[1,2-a]pyridin-6-yl)-6-methyl-3-pyridinecarbonitrile described above was stirred under reflux for 3 hours. After cooling, the solvent was removed by distillation and chloroform-water was added to the residue. The chloroform was taken by fractionation. After washing with water and drying over magnesium sulfate, chloroform was removed by distillation under reduced pressure. The residue was recrystallized from benzene-n-hexane to obtain 0.75 g of 5-(imidazo[1,2-a]pyridin-6-yl)-2-methoxy-6-methyl-3-pyridinecarbonitrile.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. customthe solvent was removed by distillation and chloroform-water
  4. additionwas added to the residue
  5. washAfter washing with water
  6. dry with materialdrying over magnesium sulfate, chloroform
  7. customwas removed by distillation under reduced pressure
  8. customThe residue was recrystallized from benzene-n-hexane

Sources & evidence

ORD record
ord-157b09f3abae40568f6ae65bcad772f7
Source dataset
uspto-grants-1988_06
Patent number
US04751227

Reaction notes

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