4-benzyloxy-1-ethyl-2-methyl-1H-benzimidazole → 1H-Benzimidazol-4-ol, 1-ethyl-2-methyl-

HRID 636472Notes

Reaction equation

HRID 636472 reaction equation
C([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([CH2:19][CH3:20])[C:13]=2[CH:12]=[CH:11][CH:10]=1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[CH2:19]([N:14]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([OH:8])[C:17]=2[N:16]=[C:15]1[CH3:18])[CH3:20]

Participants

4

Reactant 1

HCID 108017214-benzyloxy-1-ethyl-2-methyl-1H-benzimidazole

Product 1

HCID 108211611H-Benzimidazol-4-ol, 1-ethyl-2-methyl-Yield 89.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-benzyloxy-l-ethyl-2-methyl-1H-benzimidazole (370 mg) in ethyl acetate (3.7 ml) was added 10% palladium on carbon (18 mg), and the mixture was stirred for 5 hours at ambient temperature under hydrogen atmosphere. Insoluble material was filtered off, and the filtrate was concentrated in vacuo. The residue was crystallized with diisopropyl ether to give 1-ethyl-4-hydroxy-2-methyl-1H-benzimidazole (220 mg).

Workup

  1. filtrationInsoluble material was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was crystallized with diisopropyl ether

Sources & evidence

ORD record
ord-ca3f687e8afb48959acfeb3a08d99c6a
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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