HCID 178418361, compound → HCID 178430523, compound

HRID 968799Notes

Reaction equation

HRID 968799 reaction equation
[CH3:1][C:2]1[C:7]2[NH:8][CH:9]=[N:10][C:6]=2[C:5]([C:11]#[N:12])=[CH:4][C:3]=1[N+:13]([O-])=O.[H][H]>CN(C=O)C.[Pt]>[NH2:13][C:3]1[CH:4]=[C:5]([C:11]#[N:12])[C:6]2[N:10]=[CH:9][NH:8][C:7]=2[C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178430969HCID 178430969, compound

Product 1

HCID 178430523HCID 178430523, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-Methyl-6-nitro-1H-benzimidazole-4-carbonitrile (24) (1.010 g, 5.0 mmol) and Pt/C (5% Pt/C sulfided, 0.502 g, 50 wt %, C5002 Engelhard Industries) in DMF (75 mL) is hydrogenated at about 40 psi hydrogen pressure at about 50° C. over about 24 hours. The catalyst is removed from the reaction mixture by filtration through a Celite pad and the filtrate is concentrated in vacuo. The residue obtained is triturated in acetonitrile, and filtered to provide 6-Amino-7-methyl-1H-benzimidazole-4-carbonitrile (10), as a tan solid (0.768 g, 90% Yield).

Workup

  1. customThe catalyst is removed from the reaction mixture by filtration through a Celite pad
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue obtained
  4. customis triturated in acetonitrile
  5. filtrationfiltered

Sources & evidence

ORD record
ord-58f400fa5f094b26ab26f318e775f936
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

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