Trifluoroacetic acid → HCID 58508575, compound

HRID 454594Notes

Reaction equation

HRID 454594 reaction equation
FC(F)(F)C(O)=O.[OH:8][C:9]1[CH:36]=[C:35]([NH:37][CH3:38])[CH:34]=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18]C(C)(C)C)=[O:17])=[O:12]>>[OH:8][C:9]1[CH:36]=[C:35]([NH:37][CH3:38])[CH:34]=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:15]=1[C:16]([OH:18])=[O:17])=[O:12]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58508615HCID 58508615, compound

Product 1

HCID 58508575HCID 58508575, compoundYield 59.9%

Procedure

Trifluoroacetic acid (5 mL) was added to the obtained tert-butyl 2-(2-hydroxy-4-(methylamino)benzamido)-4-phenylbenzoate (0.027 g), followed by stirring at room temperature for 3 hours. The solvent was evaporated under reduced pressure, and water and ethyl acetate were added to the residue, followed by adjusting the pH to 6 with a saturated aqueous solution of sodium bicarbonate. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue, and the solid substance was collected by filtration to obtain 0.014 g of 2-(2-hydroxy-4-(methylamino)benzamido)-4-phenylbenzoic acid as a light yellow solid.

Workup

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

Sources & evidence

ORD record
ord-87f3678177b84537b43bfb48c077e768
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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