Trifluoroacetic acid → HCID 11950812, compound

HRID 2191857Notes

Reaction equation

HRID 2191857 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([CH3:36])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21]C(C)(C)C)=[O:20]>>[CH3:8][N:9]([CH3:36])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:27]=[CH:26][C:18]=1[C:19]([OH:21])=[O:20]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68963147HCID 68963147, compound

Product 1

HCID 11950812HCID 11950812, compound

Procedure

Trifluoroacetic acid 5.0 mL was added to the obtained tert-butyl 2-((2-(dimethylamino)phenyl)amino)-4-phenylbenzoate, and it was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 50-85% acetonitrile/0.1% trifluoroacetic acid aqueous solution], subsequently ethyl acetate and water were added to it, 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, the solvent was removed under reduced pressure. Hexane was added to the obtained residue, and solid matter was filtrated to give 2-((2-(dimethylamino)phenyl)amino)-4-phenylbenzoic acid 17 mg of a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-e96ac394bf0a40618cd44f49aef00380
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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