4-(4-nitro-1H-benzimidazol-1-yl)benzonitrile → 4-(4-amino-1H-benzimidazol-1-yl)benzonitrile

HRID 1051167Notes

Reaction equation

HRID 1051167 reaction equation
[N+:1]([C:4]1[C:12]2[N:11]=[CH:10][N:9]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[C:12]2[N:11]=[CH:10][N:9]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 683865734-(4-nitro-1H-benzimidazol-1-yl)benzonitrile

Product 1

HCID 683868484-(4-amino-1H-benzimidazol-1-yl)benzonitrileYield 42.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 4-(4-nitro-1H-benzimidazol-1-yl)benzonitrile (1.2 g, 4.54 mmol) in ethanol (100 mL) at rt was added Pd/C 10% (96 mg) in one portion and the mixture was stirred under a hydrogen atmosphere at normal pressure for 26 h. The suspension was filtered, and the solution was evaporated. Purification of the residue by flash chromatography yielded 4-(4-amino-1H-benzimidazol-1-yl)benzonitrile (0.45 g, 42.3%).

Workup

  1. filtrationThe suspension was filtered
  2. customthe solution was evaporated
  3. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-8906b3122d014cebb531c6eb35d2f011
Source dataset
uspto-grants-2016_07
Patent number
US09388140B2

Reaction notes

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