Ammonium formate → 4,7-dimethyl-3H-benzimidazol-5-amine

HRID 2260730Notes

Reaction equation

HRID 2260730 reaction equation
[CH3:1][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[C:5]([CH3:11])=[CH:4][C:3]=1[N+:12]([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:12][C:3]1[CH:4]=[C:5]([CH3:11])[C:6]2[N:7]=[CH:8][NH:9][C:10]=2[C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 224622214,7-Dimethyl-5-nitro-1H-benzo[d]imidazole

Product 1

HCID 183798614,7-dimethyl-3H-benzimidazol-5-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4,7-dimethyl-5-nitrobenzimidazole (1.17 g) in methanol (150 mL) is added Pd/C (10%, 0.16 g) and ammonium formate (1.31 g). The mixture is stirred at room temperature overnight, then filtered on Celite, with methanol wash of the solids. The filtrate is rotary evaporated and the residue partitioned between water and ethyl acetate. The organic layer is washed with saturated ammonium chloride, dried over magnesium sulfate, filtered and rotary evaporated to afford 5-amino-4,7-dimethylbenzimidazole as a foamy reddish solid.

Workup

  1. filtrationfiltered on Celite, with methanol
  2. washwash of the solids
  3. customThe filtrate is rotary evaporated
  4. customthe residue partitioned between water and ethyl acetate
  5. washThe organic layer is washed with saturated ammonium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customrotary evaporated

Sources & evidence

ORD record
ord-2ea90da49f2b4fa487a09076eb966005
Source dataset
uspto-grants-1995_12
Patent number
US05478858

Reaction notes

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