1-Methyl-4-nitro-1H-benzimidazole → 4-Amino-1-methylbenzimidazole

HRID 501528Notes

Reaction equation

HRID 501528 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-])=O)[C:5]=2[N:4]=[CH:3]1>CCO.[Pd]>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([NH2:11])[C:5]=2[N:4]=[CH:3]1

Participants

4

Reactant 1

HCID 15019621-Methyl-4-nitro-1H-benzimidazole

Product 1

HCID 15019774-Amino-1-methylbenzimidazoleYield 93.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-methyl-4-nitro-1H-benzimidazole [2.1 g, 12 mmol, prepared as described in Viktor Milata et. al., Org. Prep. Proced. Int. 25 (6), 703-704 (1993)] and 5% Pd/C (0.21 g) in EtOH (40 mL) was vigorously stirred under an atmosphere of hydrogen at rt overnight. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to afford the title compound (1.65 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-fd9fca2332024759bfd75888ee1080ae
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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