Benzoic acid, 2-(acetylamino)-4-nitro- → 4-Amino-2-acetamidobenzoic acid

HRID 1111311Notes

Reaction equation

HRID 1111311 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:13][C:14](=[O:16])[CH3:15])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=[O:9])([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:13][C:14](=[O:16])[CH3:15])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 70373Benzoic acid, 2-(acetylamino)-4-nitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 136983294-Amino-2-acetamidobenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture prepared by dissolving 575 mg of 4-nitro-N-acetyl-anthranilic acid in 200 ml of ethyl acetate and by mixing the resultant solution with 100 mg of a 10% Pd-C catalyst was stirred at room temperature in a hydrogen gas atmosphere for 4 hours. Then, the reaction mixture was filtered through a Celite filter to remove the catalyst, and the catalyst was washed with ethyl acetate. The total amount of the filtrate was collected and concentrated under a reduced a silica gel column chromatography. A final product consisting of 4-amino-N-acetyl-anthranilic acid was obtained in an amount of 450 mg.

Workup

  1. customA reaction mixture prepared
  2. filtrationThen, the reaction mixture was filtered through a Celite
  3. filtrationfilter
  4. customto remove the catalyst
  5. washthe catalyst was washed with ethyl acetate
  6. customThe total amount of the filtrate was collected
  7. concentrationconcentrated under
  8. customwas obtained in an amount of 450 mg

Sources & evidence

ORD record
ord-eed39d9ef2fd4c6d88231c49a4d03c29
Source dataset
uspto-grants-1990_12
Patent number
US04980287

Reaction notes

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