Ethanol → 4-(Benzylamino)-2-(4-fluoroanilino)benzoic acid

HRID 2191685Notes

Reaction equation

HRID 2191685 reaction equation
[OH-].[Na+].C(O)C.[CH2:6]([NH:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[C:16]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl-].[Na+]>C(OCC)(=O)C.C(O)(=O)C>[CH2:6]([NH:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[C:16]([NH:24][C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[CH:15]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 5234Sodium ChlorideHCID 14798Sodium Hydroxide2×HCID 57667993Methyl 4-(benzylamino)-2-(4-fluoroanilino)benzoate

Product 1

HCID 576680934-(Benzylamino)-2-(4-fluoroanilino)benzoic acidYield 73.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

10% Sodium hydroxide aqueous solution 0.82 mL was added to a suspension of ethanol 3.0 mL of methyl 4-(benzylamino)-2-(4-fluoroanilino)benzoate 0.24 g at room temperature, and it was heated and refluxed for 2 hours. After the reaction mixture was cooled to room temperature, 10% sodium hydroxide aqueous solution 0.82 mL was added, and it was heated and refluxed for 3 hours. After the reaction mixture was cooled to room temperature, acetic acid 2.0 mL, saturated sodium chloride aqueous solution 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-(benzylamino)-2-(4-fluoroanilino)benzoic acid 0.17 g of white solid.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed for 2 hours
  3. temperatureit was heated
  4. temperaturerefluxed for 3 hours
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. customcollected
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed under reduced pressure
  10. additionDiisopropyl ether and hexane were added to the obtained residue, and solid matter
  11. filtrationwas filtrated

Sources & evidence

ORD record
ord-057cd676c6bc47dfa5e94caf7ac682e1
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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