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

HRID 2191666Notes

Reaction equation

HRID 2191666 reaction equation
[OH-].[Na+].CC(O)C.[CH:7]1([O:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[C:16]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl>C(OCC)(=O)C>[CH:7]1([O:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[C:16]([NH:24][C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[CH:15]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 57668066Methyl 4-(cyclohexyloxy)-2-(4-fluoroanilino)benzoate

Product 1

HCID 576680024-(Cyclohexyloxy)-2-(4-fluoroanilino)benzoic acidYield 20.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

10% Sodium hydroxide aqueous solution 0.25 mL was added to a suspension of 2-propanol 2.0 mL of methyl 4-(cyclohexyloxy)-2-(4-fluoroanilino)benzoate 40 mg at room temperature, and it was heated and refluxed for 5 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-(cyclohexyloxy)-2-(4-fluoroanilino)benzoic acid 8 mg of white solid.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed for 5 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-0ee9a5cb7b074377be538df55908c6e4
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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