3-(Formylamino)-4-methyl-2-nitrobenzoic acid → HCID 178425875, compound

HRID 968796Notes

Reaction equation

HRID 968796 reaction equation
[CH:1]([NH:3][C:4]1[C:5]([N+:14]([O-])=O)=[C:6]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:7]([OH:9])=[O:8])=O.C(NC1C=C(C([N+]([O-])=O)=CC=1C)C(O)=O)=O>C(O)=O.[Pd]>[CH3:13][C:12]1[C:4]2[NH:3][CH:1]=[N:14][C:5]=2[C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 590163073-(Formylamino)-4-methyl-2-nitrobenzoic acidHCID 590163133-(Formylamino)-4-methyl-6-nitrobenzoic acid

Product 1

HCID 178425875HCID 178425875, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 284Formic AcidSolvent

Procedure

A mixture of 3-(Formylamino)-4-methyl-2-nitrobenzoic acid (18) and 3-(Formylamino)-4-methyl-6-nitrobenzoic acid (18b) in a ratio of about 66:34 (9.999 g, 44.56 mmol) and Pd/C (10%, 2 g, 4 mol % Pd) in 75% aqueous formic acid (120 mL, 0.5M) is heated at reflux for about 15 hours. The reaction mixture is then cooled to ambient temperature and filtered through a pad of Celite, and the filtrate is 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 (5.564 g, 98% Yield, based on amount of 3-(Formylamino)-4-methyl-2-nitrobenzoic acid (18) in the starting material mixture).

Workup

  1. temperatureis heated
  2. temperatureat reflux for about 15 hours
  3. filtrationfiltered through a pad of Celite
  4. concentrationthe filtrate is 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-ecc1027b9210468c80b005e56a78beb8
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

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