Benzoic acid, 4-nitro-2-[(trifluoroacetyl)amino]- → HCID 22152169, compound

HRID 1111307Notes

Reaction equation

HRID 1111307 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=[O:9])([O-])=O.[H][H]>C(O)C.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:13][C:14](=[O:19])[C:15]([F:16])([F:17])[F:18])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 605646Benzoic acid, 4-nitro-2-[(trifluoroacetyl)amino]-HCID 178418361HCID 178418361, compound

Product 1

HCID 22152169HCID 22152169, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

An amount of 5.24 g of 4-nitro-N-trifluoroacetyl-anthranilic acid was dissolved in 100 ml of ethyl alcohol, 2 g of a 10% palladium-carbon catalyst were added to the resultant solution, and the resultant mixture was stirred for 2.5 hours at room temperature in a hydrogen gas stream. The resultant reaction mixture was filtered through a Celite filter (trademark, made by Johns Manville Sales), and the catalyst on the Celite filter was washed with ethyl alcohol. The entire amount of the filtrate was collected, concentrated, and dry solidified under a reduced pressure, and the resultant crude product in an amount of 4.7 g was recrystallized from an ethyl alcohol-hexane or ethyl alcohol-water mixed solvent.

Workup

  1. customThe resultant reaction mixture
  2. filtrationwas filtered through a Celite
  3. filtrationfilter (trademark, made by Johns Manville Sales)
  4. filtrationthe catalyst on the Celite filter
  5. washwas washed with ethyl alcohol
  6. customThe entire amount of the filtrate was collected
  7. concentrationconcentrated
  8. customdry
  9. customthe resultant crude product in an amount of 4.7 g was recrystallized from an ethyl alcohol-hexane or ethyl alcohol-water mixed solvent

Sources & evidence

ORD record
ord-63336d5b39a9430db8f3c0346f555abb
Source dataset
uspto-grants-1990_12
Patent number
US04980287

Reaction notes

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