5-Nitrobenzimidazole → 5-Aminobenzimidazole

HRID 2268941Notes

Reaction equation

HRID 2268941 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=1)([O-])=O>C1COCC1.[Pd]>[NH2:1][C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 71955-Nitrobenzimidazole

Product 1

HCID 136235-AminobenzimidazoleYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-nitrobenzimidazole (1 g, 6.13 mmol, 1 eq) in THF (100 mL) was added 10% palladium on carbon (385 mg). The flask was purged with H2 and the mixture was stirred under a balloon of H2 for several hours. The flask was purged with N2. The catalyst was filtered and washed with MeOH. The solution was concentrated under reduced pressure giving 800 mg of the desired product.

Workup

  1. customThe flask was purged with H2
  2. customThe flask was purged with N2
  3. filtrationThe catalyst was filtered
  4. washwashed with MeOH
  5. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-70505ca0e1104fa0a183307104e2ccd0
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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