Hydrochloric Acid → 4-Anilino-2-(4-fluoroanilino)benzoic acid

HRID 2191683Notes

Reaction equation

HRID 2191683 reaction equation
C(O)C.[NH:4]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[C:13]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].Cl>C(OCC)(=O)C.O>[NH:4]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([OH:17])=[O:16])=[C:13]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[CH:12]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 57667985Methyl 4-anilino-2-(4-fluoroanilino)benzoate

Product 1

HCID 576680774-Anilino-2-(4-fluoroanilino)benzoic acidYield 100.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of ethanol 2.0 mL of methyl 4-anilino-2-(4-fluoroanilino)benzoate 0.25 g was added water 1.0 mL solution of sodium hydroxide 0.060 g at room temperature, and it was heated and refluxed for 2 hours. After the reaction mixture was cooled to room temperature,1.0 mol/L hydrochloric acid and ethyl acetate were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. Diisopropyl ether and hexane were added to the obtained residue, and solid matter was filtrated to give 4-anilino-2-(4-fluoroanilino)benzoic acid 0.24 g of white solid.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed for 2 hours
  3. customThe organic layer was separated
  4. customthe solvent was removed under reduced pressure
  5. additionDiisopropyl ether and hexane were added to the obtained residue, and solid matter
  6. filtrationwas filtrated

Sources & evidence

ORD record
ord-83161d65338d4f10b63cd3c24e2270de
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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