Sodium Hydroxide → 4-(Phenylamino)benzoic acid

HRID 1777567Notes

Reaction equation

HRID 1777567 reaction equation
[C:1]1([NH:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O.O1CCOCC1>[C:1]1([NH:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 614877Methyl 4-anilinobenzoate

Product 1

HCID 2923314-(Phenylamino)benzoic acidYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 4-(phenylamino)benzoate (0.080 g; 0.352 mmol) was added to a mixture of NaOH in water (0.6 mL; 2M) and dioxane (0.6 mL) and stirred vigorously at room temperature overnight. The resulting mixture was concentrated in vacuo and extracted with dichloromethane. The aqueous layer was acidified with a solution of hydrogen chloride 6M and the precipitated product was collected by filtration and used without further purifications to yield 0.048 g (64%) of the title compound as a white solid which was used without further purifications.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. extractionextracted with dichloromethane
  3. filtrationthe precipitated product was collected by filtration

Sources & evidence

ORD record
ord-69987c23acac4a4c87c1f8d12e8eab7e
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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