Sodium Hydroxide → 1-Methyl-1H-benzimidazole-2-carboxylic acid

HRID 1850287Notes

Reaction equation

HRID 1850287 reaction equation
C[O:2][C:3]([C:5]1[N:9]([CH3:10])[C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[N:6]=1)=[O:4].[OH-].[Na+]>CO.O>[CH3:10][N:9]1[C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[N:6]=[C:5]1[C:3]([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2802598Methyl 1-methyl-1H-benzimidazole-2-carboxylate

Product 1

HCID 31597051-Methyl-1H-benzimidazole-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-methyl-1H-benzoimidazole-2-carboxylic acid methyl ester (81) (190 mg, 1.0 mmol) and NaOH (80 mg, 2.0 mmol) in MeOH/H2O (1:1, 20 mL) was stirred at 50° C. for 1 h. The mixture was concentrated, then diluted with water (15 mL), adjusted pH=2 with concentrated HCl. Then the precipitate was formed and filtered, washed with water and dried to give 1-methyl-1H-benzoimidazole-2-carboxylic acid (82) (176 mg, 1.0 mmol, yield 100%)

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with water (15 mL)
  3. customThen the precipitate was formed
  4. filtrationfiltered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-6da0d012ac50452984f740ec7d7262d2
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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