Formic Acid → 6-Methoxy-7-methyl-1H-benzimidazole

HRID 1648292Notes

Reaction equation

HRID 1648292 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:11])=[C:5]([NH2:10])[C:6]([NH2:9])=[CH:7][CH:8]=1.[CH:12](O)=O>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[NH:9][CH:12]=[N:10][C:5]=2[C:4]=1[CH3:11]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 59245497433-22-2

Product 1

HCID 199193886-Methoxy-7-methyl-1H-benzimidazoleYield 84%

Conditions

Temperature
60 °C

Procedure

A mixture of 4-methoxy-3-methyl-l,2-benzenediamine (2.8 g, 18A mmol) and formic acid (30 mL) was heated at 60° C. for 30 minutes. The formic acid was removed under reduced pressure and the product was partitioned between chloroform and water containing sufficient sodium hydroxide to basify the solution. After evaporation of the solvent the crude product was chromatographed (methanol:chloroform) to give 2.55 g (84%) of 5-methoxy-4-methyl-1H-benzimidazole.

Workup

  1. customThe formic acid was removed under reduced pressure
  2. customthe product was partitioned between chloroform and water containing sufficient sodium hydroxide
  3. customAfter evaporation of the solvent the crude product
  4. customwas chromatographed (methanol:chloroform)

Sources & evidence

ORD record
ord-6be311e07a5947c88132b29c86c14593
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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