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

HRID 751048Notes

Reaction equation

HRID 751048 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.[H][H]>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

5

Reactant 2

HCID 15019621-Methyl-4-nitro-1H-benzimidazoleHCID 178418361HCID 178418361, compound

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 atmoshphere of hydrogen at rt overnight. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to afford the tiltle compound (1.65 g).

Workup

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

Sources & evidence

ORD record
ord-af6de576f52b43a29526c64c6d613f25
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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