5,6-Dinitro-1H-benzo[d]imidazole → 1H-benzimidazole-5,6-diamine

HRID 629687Notes

Reaction equation

HRID 629687 reaction equation
[N+:1]([C:4]1[C:12]([N+:13]([O-])=O)=[CH:11][C:7]2[NH:8][CH:9]=[N:10][C:6]=2[CH:5]=1)([O-])=O.[H][H]>CCO.[Pd]>[NH2:13][C:12]1[C:4]([NH2:1])=[CH:5][C:6]2[NH:10][CH:9]=[N:8][C:7]=2[CH:11]=1

Participants

5

Reactant 2

HCID 34744945,6-Dinitro-1H-benzo[d]imidazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 27731931H-benzimidazole-5,6-diamineYield 67.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product obtained in Step 1 (2.5 g, 12 mmol) and Pd/C (0.5 g) were dissolved in EtOH (50 mL), reacted in a Parr hydrogenation apparatus at room temperature and hydrogen gas pressure until the reaction is completed. The catalyst was removed by filtration, the filtrate was concentrated under vacuum, diluted with ethyl acetate, washed with water, dried, and concentrated under vacuum to obtain a product (1.2 g, 66.7%).

Workup

  1. customreacted in a Parr hydrogenation apparatus at room temperature
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under vacuum
  4. additiondiluted with ethyl acetate
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-74186dd3f1984af89353a048e683b407
Source dataset
uspto-grants-2016_04
Patent number
US09315513B2

Reaction notes

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