Methanol → 6-Methoxy-1-methyl-1H-benzimidazole

HRID 2091219Notes

Reaction equation

HRID 2091219 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-])=O)=[C:7]([CH:10]=1)[NH:8][CH3:9].[CH3:14]O>[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]=[CH:9][N:8]([CH3:14])[C:7]=2[CH:10]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 153056Benzenamine, 5-methoxy-N-methyl-2-nitro-

Product 1

HCID 118050756-Methoxy-1-methyl-1H-benzimidazoleYield 60%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution (200 mL) of 5-methoxy-N-methyl-2-nitroaniline (6.30 g) synthesized above in methanol was added 10% palladium/carbon (1.00 g) and the mixture was stirred under hydrogen atmosphere overnight at room temperature. Palladium/carbon was filtered off, and the filtrate was concentrated. A solution (150 mL) of the residue in formic acid was stirred overnight with heating under reflux, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (25% ethyl acetate/petroleum ether) to give the title object compound (4.07 g, 60%) as a white solid.

Workup

  1. filtrationPalladium/carbon was filtered off
  2. concentrationthe filtrate was concentrated
  3. stirringA solution (150 mL) of the residue in formic acid was stirred overnight
  4. temperaturewith heating
  5. temperatureunder reflux
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (25% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-e976256f9a7d470ea1c73ae16c17e53b
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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