Trifluoroacetic acid → 4-Phenyl-2-(4-phenylpyridine-2-carboxamido)benzoic acid

HRID 454776Notes

Reaction equation

HRID 454776 reaction equation
FC(F)(F)C(O)=O.[C:8]1([C:14]2[CH:26]=[CH:25][C:17]([C:18]([O:20]C(C)(C)C)=[O:19])=[C:16]([NH:27][C:28]([C:30]3[CH:35]=[C:34]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:33]=[CH:32][N:31]=3)=[O:29])[CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:8]1([C:14]2[CH:26]=[CH:25][C:17]([C:18]([OH:20])=[O:19])=[C:16]([NH:27][C:28]([C:30]3[CH:35]=[C:34]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH:33]=[CH:32][N:31]=3)=[O:29])[CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58508724Tert-butyl 4-phenyl-2-(4-phenylpyridine-2-carboxamido)benzoate

Product 1

HCID 585089074-Phenyl-2-(4-phenylpyridine-2-carboxamido)benzoic acidYield 89.2%

Procedure

Trifluoroacetic acid (5 mL) was added to the obtained tert-butyl 4-phenyl-2-(4-phenylpyridine-2-carboxamido)benzoate (64 mg), followed by stirring at room temperature for 3 hours. The solvent was evaporated under reduced pressure, and ethyl acetate and water were added to the obtained residue. After adjusting the pH to 6.5 with a saturated aqueous solution of sodium bicarbonate, the organic layer was separated, washed with water and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration to obtain 50 mg of 4-phenyl-2-(4-phenylpyridine-2-carboxamido)benzoic acid as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and ethyl acetate and water
  2. additionwere added to the obtained residue
  3. customthe organic layer was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. additionDiisopropyl ether was added to the obtained residue
  8. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-a68ca11a4c074c5b8bc80ff71709218a
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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