Amfenac → Sodium 2-amino-3-benzoylphenylacetate Dihydrate

HRID 442546Notes

Reaction equation

HRID 442546 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([OH:19])=[O:18].[OH-:20].[Na+:21]>O>[OH2:15].[OH2:20].[NH2:1][C:2]1[C:7]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([O-:19])=[O:18].[Na+:21]

Participants

4

Reactant 2

HCID 2136AmfenacHCID 14798Sodium Hydroxide

Product 1

HCID 68667642Sodium 2-amino-3-benzoylphenylacetate DihydrateYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.6 g. of (2-amino-3-benzoylphenyl)acetic acid and sodium hydroxide (0.1 mole) in 25 ml. of water was stirred for approximately 10 min. and then heated to reflux under nitrogen. The reaction mixture was then cooled and filtered. The filtrate was evaporated down to approximately 2 ml., refiltered and a large volume of acetone added to the filtrate to precipitate the product as bright yellow flakes. Yield 70%.

Workup

  1. additionA mixture of 2.6 g
  2. temperatureheated
  3. temperatureto reflux under nitrogen
  4. temperatureThe reaction mixture was then cooled
  5. filtrationfiltered
  6. customThe filtrate was evaporated down to approximately 2 ml
  7. additiona large volume of acetone added to the filtrate
  8. customto precipitate the product as bright yellow flakes

Sources & evidence

ORD record
ord-b520ef586a7f468e8afe0398c2df3352
Source dataset
uspto-grants-1977_08
Patent number
US04045576

Reaction notes

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