Trifluoroacetic acid → 4-(4-(Dimethylamino)phenyl)-2-(4-fluoroanilino)benzoic acid

HRID 2191769Notes

Reaction equation

HRID 2191769 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([CH3:37])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:28]=[CH:27][C:19]([C:20]([O:22]C(C)(C)C)=[O:21])=[C:18]([NH:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[CH:17]=2)=[CH:12][CH:11]=1>>[CH3:8][N:9]([CH3:37])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:28]=[CH:27][C:19]([C:20]([OH:22])=[O:21])=[C:18]([NH:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[CH:17]=2)=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68965065Tert-butyl 4-(4-(dimethylamino)phenyl)-2-(4-fluoroanilino)benzoate

Product 1

HCID 576680724-(4-(Dimethylamino)phenyl)-2-(4-fluoroanilino)benzoic acid

Procedure

Trifluoroacetic acid 5.0 mL was added to the obtained tert-butyl 4-(4-(dimethylamino)phenyl)-2-(4-fluoroanilino)benzoate, and it was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, ethyl acetate and water were added, and it was adjusted to pH6.5 with saturated sodium hydrogen carbonate aqueous solution. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Diisopropyl ether was added to the obtained residue, and solid matter was filtrated to give 4-(4-(dimethylamino)phenyl)-2-(4-fluoroanilino)benzoic acid 33 mg of a yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure, ethyl acetate and water
  2. additionwere added
  3. customThe organic layer was separated
  4. washafter washing with saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure
  6. additionDiisopropyl ether was added to the obtained residue, and solid matter
  7. filtrationwas filtrated

Sources & evidence

ORD record
ord-73cc354613854b77a407f483c433db2e
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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