Dimethylformamide → 1-Methyl-1H-benzimidazole-5-carboxylic acid

HRID 858293Notes

Reaction equation

HRID 858293 reaction equation
[CH3:1][NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-])=O.[H][H].[CH3:17]N(C=O)C>[Pd]>[CH3:1][N:2]1[C:3]2[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=2[N:12]=[CH:17]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2834754-(Methylamino)-3-nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 49130631-Methyl-1H-benzimidazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

25.0 g of 4-methylamino-3-nitrobenzoic acid, dissolved in 200 ml DMF, are hydrogenated for 5 hours at a hydrogen pressure of 30 psi with the addition of 2.5 g of palladium on activated charcoal (10%). The catalyst is suction filtered and the solvent is distilled off. The residue is stirred with diethyl ether, suction filtered and dried. The crude product thus obtained (19.7 g) is refluxed for 2 hours in 250 ml formic acid. After the solvent has been distilled off the residue is stirred with diethyl ether, suction filtered and dried.

Workup

  1. filtrationfiltered
  2. distillationthe solvent is distilled off
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-8717d5d8a84f4693bc5a048cf907170e
Source dataset
uspto-grants-2006_12
Patent number
US07148249B2

Reaction notes

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