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

HRID 1936579Notes

Reaction equation

HRID 1936579 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 1.17 g of 4,7-dimethyl-5-nitrobenzimidazole in 150 mL of methanol are added 160 mg of palladium-on-carbon (10%) and 1.31 g of ammonium formate. The mixture is stirred at room temperature overnight, then filtered on Celite, with a 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 a 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-310503ca0579403898359a35541d33d2
Source dataset
uspto-grants-2002_05
Patent number
US06391878B2

Reaction notes

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