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

HRID 6354Notes

Reaction equation

HRID 6354 reaction equation
C(C1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[N:11]=[C:10]2[CH3:18])=[CH:5][CH:4]=1)#N.[OH-:19].[Na+].[CH2:21]([OH:23])[CH3:22]>>[CH3:18][C:10]1[N:9]([C:6]2[CH:7]=[CH:8][C:22]([C:21]([OH:19])=[O:23])=[CH:4][CH:5]=2)[C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N:11]=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 1-(4-cyanophenyl)-2-methylimidazo[4,5-c]pyridine (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-c0a37bba41f04afd9a67999b126b0e4c
Source dataset
uspto-grants-1993_09
Patent number
US05248681

Reaction notes

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