Water → 2-(4-Fluoroanilino)-4-(isoquinolin-4-yl)benzoic acid

HRID 2191661Notes

Reaction equation

HRID 2191661 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:38]=[CH:37][C:12]([NH:13][C:14]2[CH:26]=[C:25]([C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=[N:29][CH:28]=3)[CH:24]=[CH:23][C:15]=2[C:16]([O:18]C(C)(C)C)=[O:17])=[CH:11][CH:10]=1.O.[OH-].[Na+]>C(OCC)(=O)C>[F:8][C:9]1[CH:38]=[CH:37][C:12]([NH:13][C:14]2[CH:26]=[C:25]([C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=[N:29][CH:28]=3)[CH:24]=[CH:23][C:15]=2[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 68958084HCID 68958084, compound

Product 1

HCID 576679632-(4-Fluoroanilino)-4-(isoquinolin-4-yl)benzoic acidYield 52.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic acid 3.0 mL solution of tert-butyl 2-(4-fluoroanilino)-4-(isoquinolin-4-yl)benzoate 110 mg was stirred at room temperature for 1 hour. Water and ethyl acetate were added to the reaction mixture, and it was adjusted to pH6.0 with 1.0 mol/L sodium hydroxide aqueous solution. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue, and solid matter was filtrated to give 2-(4-fluoroanilino)-4-(isoquinolin-4-yl)benzoic acid 50 mg of pale green solid.

Workup

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

Sources & evidence

ORD record
ord-5fe0d9119cd94ae4b3bbdd1bc051b248
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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