Ethanol → 4-(2-Methyl-1H-imidazo[4,5-C]pyridin-1-YL)benzoic acid

HRID 1085143Notes

Reaction equation

HRID 1085143 reaction equation
[CH3:1][C:2]1[N:3]([C:11]2[CH:18]=[CH:17]C(C#N)=[CH:13][CH:12]=2)[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.[OH-:19].[Na+].[CH2:21]([OH:23])[CH3:22]>>[CH3:1][C:2]1[N:3]([C:11]2[CH:18]=[CH:17][C:22]([C:21]([OH:19])=[O:23])=[CH:13][CH:12]=2)[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 106811874-(2-Methyl-1H-imidazo[4,5-c]pyridin-1-yl)benzonitrile

Product 1

HCID 104674374-(2-Methyl-1H-imidazo[4,5-C]pyridin-1-YL)benzoic acid

Conditions

Temperature
0 °C

Procedure

A mixture of 4-(2-methylimidazo[4,5-c]pyrid-1-yl)benzonitrile (12.0 g, 51.3 mmol) and 40% aqueous sodium hydroxide (55 ml) in absolute ethanol (55 ml) was heated at reflux for 11/2 hours. The solvent was removed under reduced pressure, and the brown residue was dissolved in water. The solution was chilled to 0° C. by the addition of ice. Glacial acetic acid (ca 33 ml) was added slowly. The buff solid which precipitated was filtered off, washed with water, and dried in vacuo at 70° C. Yield 9.14 g (70%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 11/2 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe brown residue was dissolved in water
  5. additionGlacial acetic acid (ca 33 ml) was added slowly
  6. customThe buff solid which precipitated
  7. filtrationwas filtered off
  8. washwashed with water
  9. customdried in vacuo at 70° C

Sources & evidence

ORD record
ord-35d0f6e38701427a9e404141a1f6165c
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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