HCID 86637890, compound → ethyl (4-hydroxy-2-methyl-1H-benzimidazol-1-yl)acetate

HRID 2389349Notes

Reaction equation

HRID 2389349 reaction equation
C([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:13]=2[CH:12]=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>CCO.C1COCC1.[Pd]>[OH:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 2

HCID 86637890HCID 86637890, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86637909ethyl (4-hydroxy-2-methyl-1H-benzimidazol-1-yl)acetateYield 93.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [4-(benzyloxy)-2-methyl-1H-benzimidazol-1-yl]acetate (2.57 g) in a mixture of EtOH (25.7 mL) and THF (12.9 mL) was added 10% palladium on carbon (50% wet, 0.78 g) at ambient temperature, and the resultant mixture was hydrogenated under atmospheric pressure of hydrogen for 2 hours. The catalyst was removed by filtration and evaporated in vacuo to give crude solid. The crude solid was recrystallized from solvent (EtOAc:n-hexane) to give ethyl (4-hydroxy-2-methyl-1H-benzimidazol-1-yl)acetate (1.73 g) as a white solid.

Workup

  1. customThe catalyst was removed by filtration
  2. customevaporated in vacuo
  3. customto give crude solid
  4. customThe crude solid was recrystallized from solvent (EtOAc:n-hexane)

Sources & evidence

ORD record
ord-6b8cfe2297b444ab816c52ba34203cd1
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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