Methanol → 4-[(trifluoroacetyl)amino]benzoic acid

HRID 2380719Notes

Reaction equation

HRID 2380719 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.CO.C(N(CC)CC)C.[F:20][C:21]([F:28])([F:27])[C:22](OCC)=[O:23]>CCOC(C)=O>[F:20][C:21]([F:28])([F:27])[C:22]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[O:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 9784-Aminobenzoic AcidHCID 8471TriethylamineHCID 9794Ethyl trifluoroacetate

Product 1

HCID 2890744-[(trifluoroacetyl)amino]benzoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of p-aminobenzoic acid in MeOH (500 mg, 3.65 mmol) was treated with 1.0 eq triethylamine (3.65 mmol, 509 μl) followed by 1.1 eq trifluoroacetic acid, ethyl ester (4.015 mmol, 478 μl). The solution was stirred overnight. The solution was diluted with EtOAc, washed with 5% KHSO4, followed by brine. The solution was dried over MgSO4 and solvent was removed by evaporation. The residue was purified by recrystallization in EtOAc/Hexane to afford eggshell-colored glossy plates (265 mg (31%), C9H6F3NO3).

Workup

  1. washwashed with 5% KHSO4
  2. dry with materialThe solution was dried over MgSO4 and solvent
  3. customwas removed by evaporation
  4. customThe residue was purified by recrystallization in EtOAc/Hexane
  5. customto afford eggshell-colored glossy plates (265 mg (31%), C9H6F3NO3)

Sources & evidence

ORD record
ord-d57d20effe0840a0b5e26d243d4ec3a6
Source dataset
uspto-grants-1994_11
Patent number
US05369123

Reaction notes

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