Sodium Hydroxide → 4-(3-Fluorophenylamino)benzoic acid

HRID 1777580Notes

Reaction equation

HRID 1777580 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>O.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67974249methyl 4-(3-Fluorophenylamino)benzoate

Product 1

HCID 113906104-(3-Fluorophenylamino)benzoic acidYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 4-(3-fluorophenylamino)benzoate (0.110 g; 0.448 mmol) was added to a mixture of NaOH in water (1 mL; 2M) and dioxane (1 mL) and stirred vigorously at room temperature overnight. The resulting mixture was concentrated under reduced pressure and dissolved in water. The aqueous layer was acidified with a solution of hydrogen chloride 6M and the precipitated product was collected by filtration to yield 0.040 g (70%) of the title compound as a grey solid which was used without further purification.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. dissolutiondissolved in water
  3. filtrationthe precipitated product was collected by filtration

Sources & evidence

ORD record
ord-c1a35abf77e6499b8d376ad64963254a
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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