Trifluoroacetic acid → 4-Phenyl-2-(5-phenylpyridine-2-carboxamido)benzoic acid

HRID 454767Notes

Reaction equation

HRID 454767 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]=[CH:34][C:33]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[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]=[CH:34][C:33]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)=[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 58508956Tert-butyl 4-phenyl-2-(5-phenylpyridine-2-carboxamido)benzoate

Product 1

HCID 585086214-Phenyl-2-(5-phenylpyridine-2-carboxamido)benzoic acidYield 93.5%

Procedure

Trifluoroacetic acid (5 mL) was added to the obtained tert-butyl 4-phenyl-2-(5-phenylpyridine-2-carboxamido)benzoate (0.11 g), followed by stirring at room temperature for 4 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 90 mg of 4-phenyl-2-(5-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-d39c22690e5b44b8af59805e4242d073
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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