Formic Acid → HCID 178425875, compound

HRID 968792Notes

Reaction equation

HRID 968792 reaction equation
[NH2:1][C:2]1[C:3]([N+:12]([O-])=O)=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[CH:15](O)=O>[Pd]>[CH3:11][C:10]1[C:2]2[NH:1][CH:15]=[N:12][C:3]=2[C:4]([C:5]([OH:7])=[O:6])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 50773353-Amino-4-methyl-2-nitrobenzoic acid

Product 1

HCID 178425875HCID 178425875, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 3-amino-4-methyl-2-nitrobenzoic acid (16) (6.883 g, 35.10 mmol), 10% Pd/C [0.3 g, 10% dry Pd/C] and 75% aqueous formic acid (60 mL) is heated to reflux for about 15 hours. The reaction mixture is then cooled to ambient temperature and filtered through a pad of Celite, and the resulting filtrate concentrated in vacuo to a beige solid. The solids are triturated in hot methanol (50 mL), cooled slowly to ambient temperature, and filtered to give 7-Methyl-1H-benzimidazole-4-carboxylic Acid (22), as beige solid (5.26 g, 85% Yield).

Workup

  1. temperatureis heated
  2. temperatureto reflux for about 15 hours
  3. filtrationfiltered through a pad of Celite
  4. concentrationthe resulting filtrate concentrated in vacuo to a beige solid
  5. customThe solids are triturated in hot methanol (50 mL)
  6. temperaturecooled slowly to ambient temperature
  7. filtrationfiltered

Sources & evidence

ORD record
ord-e018647eec924f3fa6e9013f2822ea05
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

Loading…