4-benzyloxy-2-methoxy-1-methyl-1H-benzimidazole → 4-hydroxy-2-methoxy-1-methyl-1H-benzimidazole

HRID 1871101Notes

Reaction equation

HRID 1871101 reaction equation
C([O:8][C:9]1[C:17]2[N:16]=[C:15]([O:18][CH3:19])[N:14]([CH3:20])[C:13]=2[CH:12]=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO>[OH:8][C:9]1[C:17]2[N:16]=[C:15]([O:18][CH3:19])[N:14]([CH3:20])[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 107543614-benzyloxy-2-methoxy-1-methyl-1H-benzimidazole

Product 1

HCID 106548994-hydroxy-2-methoxy-1-methyl-1H-benzimidazoleYield 34.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-benzyloxy-2-methoxy-1-methyl-1H-benzimidazole (254.8 mg) and 10% palladium on carbon (25 mg) in methanol (2.5 ml) was stirred for 7 hours at ambient temperature under hydrogen atmosphere. Insoluble material was filtered off, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate:n-hexane=3:1, V/V) to give 4-hydroxy-2-methoxy-1-methyl-1H-benzimidazole (58.7 mg).

Workup

  1. filtrationInsoluble material was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (ethyl acetate:n-hexane=3:1, V/V)

Sources & evidence

ORD record
ord-203c44a9328d428f9250a6885e578114
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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