Hydrochloric Acid → 2-(4-Fluoroanilino)-4-(3-phenylpropyl)benzoic acid

HRID 2191695Notes

Reaction equation

HRID 2191695 reaction equation
[OH-].[Na+].C(O)C.[F:6][C:7]1[CH:32]=[CH:31][C:10]([NH:11][C:12]2[CH:21]=[C:20]([CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:19]=[CH:18][C:13]=2[C:14]([O:16]C)=[O:15])=[CH:9][CH:8]=1.Cl>C(OCC)(=O)C>[F:6][C:7]1[CH:32]=[CH:31][C:10]([NH:11][C:12]2[CH:21]=[C:20]([CH2:22][CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:19]=[CH:18][C:13]=2[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 57668036Methyl 2-(4-fluoroanilino)-4-(3-phenylpropyl)benzoate

Product 1

HCID 576678062-(4-Fluoroanilino)-4-(3-phenylpropyl)benzoic acidYield 72.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

10% Sodium hydroxide aqueous solution 0.2 mL was added to a suspension of ethanol 2.0 mL of methyl 2-(4-fluoroanilino)-4-(3-phenylpropyl)benzoate 0.10 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. Hexane was added to the obtained residue, and solid matter was filtrated to give 2-(4-fluoroanilino)-4-(3-phenylpropyl)benzoic acid 70 mg 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. additionHexane was added to the obtained residue, and solid matter
  6. filtrationwas filtrated

Sources & evidence

ORD record
ord-836c67c015324e0c95f4331d2f132c96
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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