HCID 178432210, compound → HCID 178432204, compound

HRID 1936582Notes

Reaction equation

HRID 1936582 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:10]([CH3:11])=[C:9]([N+:12]([O-])=O)[CH:8]=[CH:7][C:5]=2[N:6]=1>CO.[Pd]>[NH2:12][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([CH3:1])[NH:3][C:4]=2[C:10]=1[CH3:11]

Participants

4

Reactant 1

HCID 178432210HCID 178432210, compound

Product 1

HCID 178432204HCID 178432204, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 700 mg of 2,4-dimethyl-5-nitrobenzimidazole in 50 mL of methanol is added a catalytic amount of palladium-on-carbon. The resulting suspension is stirred at room temperature under hydrogen at atmospheric pressure for 15 hours. The reaction mixture is filtered on Celite with a methanol wash of the solids and the filtrate is concentrated. The residue is purified by flash column chromatography on silica gel, eluting with 5% methanol/ethyl acetate to provide 565 mg of 5-amino-2,4-dimethybenzimidazole as a tan solid.

Workup

  1. filtrationThe reaction mixture is filtered on Celite with a methanol
  2. washwash of the solids
  3. concentrationthe filtrate is concentrated
  4. customThe residue is purified by flash column chromatography on silica gel
  5. washeluting with 5% methanol/ethyl acetate

Sources & evidence

ORD record
ord-b4b0ae0dfa8c44b1b6e2518f5c2e16b7
Source dataset
uspto-grants-2002_05
Patent number
US06391878B2

Reaction notes

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