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

HRID 1708556Notes

Reaction equation

HRID 1708556 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]>O>[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

5

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 acidYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(2-methylimidazo[4,5-c]pyrid-1-yl)benzonitrile (see EP-0310386) (12.0 g, 51.3 mmol) and sodium hydroxide (22.0 g, 0.55 mmol) in a mixture of ethanol (55 ml) and water (55 ml) was heated under nitrogen at reflux for 1.5 hours, cooled and concentrated under reduced pressure. The brown residue was dissolved in ice-water and glacial acetic acid (33 ml) was added. The resulting precipitate was collected, washed with water and dried under vacuum at 70° C. to give the title compound (9.1 g, 70%) as a buff coloured solid which as characterised by its 1H-NMR spectrum. 1H NMR (DMSO-d6), 2.50(3H,s), 7.25(1H,d,J=5 Hz), 7.72(2H,d,J=8 Hz), 8.16(2H,d,J=8 Hz), 8.30(1H,d,J=5 Hz), 8.92(1H,s).

Workup

  1. temperaturewas heated under nitrogen
  2. temperatureat reflux for 1.5 hours
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe brown residue was dissolved in ice-water
  6. additionglacial acetic acid (33 ml) was added
  7. customThe resulting precipitate was collected
  8. washwashed with water
  9. customdried under vacuum at 70° C.

Sources & evidence

ORD record
ord-7d5b5d729fa94174acd419ddb0416c71
Source dataset
uspto-grants-1994_10
Patent number
US05358953

Reaction notes

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