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

HRID 1381672Notes

Reaction equation

HRID 1381672 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-55582e5e48f8409e90eb780d6ea7cc0c
Source dataset
uspto-grants-1989_02
Patent number
US04803276

Reaction notes

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