Hydrochloric Acid → 3-(benzoylamino)benzoic acid

HRID 2086781Notes

Reaction equation

HRID 2086781 reaction equation
[OH-].[Na+].[C:3]([NH:11][C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=1)[C:15]([O:17]CC)=[O:16])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>C(O)C.O1CCOCC1>[C:3]([NH:11][C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=1)[C:15]([OH:17])=[O:16])(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 670250Ethyl 3-benzamidobenzoate

Product 1

HCID 2566173-(benzoylamino)benzoic acidYield 95.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

4N Aqueous solution of sodium hydroxide (2 ml) was added to a solution of ethyl 3-(benzoylamino)benzoate (695 mg) in ethanol (5 ml) and 1,4-dioxane (5 ml). After stirred at 50° C. for 1 hour, the mixture was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with dilute hydrochloric acid and brine, dried over magnesium sulfate and concentrated to give 3-(benzoylamino)benzoic acid (595 mg) as solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with dilute hydrochloric acid and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-713068543c8f425dbf5f9f7914a20d12
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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