Sodium Hydroxide → 4-[(1-methyl-1H-benzoimidazol-2-yl)methyl]benzoic acid

HRID 1716844Notes

Reaction equation

HRID 1716844 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=1.[OH-].[Na+]>CO>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59468706Methyl 4-((1-Methyl-1H-benzimidazol-2-yl)methyl)benzoate

Product 1

HCID 686653304-[(1-methyl-1H-benzoimidazol-2-yl)methyl]benzoic acidYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-[(1-methyl-1H-benzimidazol-2-yl)methyl]benzoate (7.0 g, 25 mmol) in methanol was treated with 2.5 N sodium hydroxide, heated at reflux temperature for 2 h, cooled to room temperature and concentrated in vacuo. The residue was dissolved in water and acidified with 6N HCl solution and filtered. The filtercake was air dried to afford 4-[(1-methyl-1H-benzoimidazol-2-yl)methyl]benzoic acid in 81% yield; 1H NMR (400 MHz, DMSO-d6): 7.90 (d, J=8 Hz, 2H), 7.57 (d, J=8 Hz, 1H), 7.49 (d, J=8 Hz, 1H), 7.40 (d, J=8 Hz, 2H), 7.17-7.20 (m, 2H), 4.39 (s, 2H), 3.70 (s, 3H). LCMS (ESI+) 276 (MH+).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in water
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-435818da85454b8c995548461979adde
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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