Sodium Hydroxide → 3-Anilinobenzoic acid

HRID 1777571Notes

Reaction equation

HRID 1777571 reaction equation
[C:1]1([NH:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11]([O:13]CC)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O.O1CCOCC1>[C:1]1([NH:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11]([OH:13])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69991060Ethyl 3-(phenylamino)benzoate

Product 1

HCID 128503413-Anilinobenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 3-(phenylamino)benzoate (0.175 g; 0.725 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 in vacuo and extracted with dichloromethane. The aqueous layer was acidified with a 6N solution of hydrochloric acid in water. The precipitated product was collected by filtration to yield 0.155 g (quantitative) of the title compound as a grey solid which was used without further purification.

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-d8a8fc7290934e9b9f24ba272fa6ebcd
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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