Trifluoroacetic acid → 2-(Benzamido)-4-(4-(dimethylamino)phenyl)benzoic acid

HRID 1673465Notes

Reaction equation

HRID 1673465 reaction equation
FC(F)(F)C(O)=O.[C:8]([NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([N:36]([CH3:38])[CH3:37])=[CH:32][CH:31]=2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21]C(C)(C)C)=[O:20])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:8]([NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:31]=[CH:32][C:33]([N:36]([CH3:38])[CH3:37])=[CH:34][CH:35]=2)[CH:27]=[CH:26][C:18]=1[C:19]([OH:21])=[O:20])(=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67344424Tert-butyl 2-(benzamido)-4-(4-(dimethylamino)phenyl)benzoate

Product 1

HCID 578793172-(Benzamido)-4-(4-(dimethylamino)phenyl)benzoic acid

Procedure

5.0 mL of trifluoroacetic acid was added to the obtained tert-butyl 2-(benzamido)-4-(4-(dimethylamino)phenyl)benzoate and stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure, ethyl acetate and water were added and pH was adjusted to pH 6.5 with a saturated sodium hydrogen carbonate aqueous solution. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. Methanol was added to the obtained residue and a solid substance was separated by filtration to obtain 3.8 mg of 2-(benzamido)-4-(4-(dimethylamino)phenyl)benzoic acid as pale yellow solid.

Workup

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

Sources & evidence

ORD record
ord-319ca271b91b491e9439b5b82040f7fb
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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