Amfenac → Ethyl (2-amino-3-benzoylphenyl)acetate

HRID 442547Notes

Reaction equation

HRID 442547 reaction equation
[Na].[NH2:2][C:3]1[C:8]([C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:17][C:18]([OH:20])=[O:19].CN(C)C=O.[CH2:26](I)[CH3:27]>O>[NH2:2][C:3]1[C:8]([C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:17][C:18]([O:20][CH2:26][CH3:27])=[O:19]

Participants

6

Reactant 4

HCID 2136AmfenacHCID 6228DimethylformamideHCID 6340IodoethaneHCID 5360545Sodium

Product 1

HCID 12901249Ethyl (2-amino-3-benzoylphenyl)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.5 g. (0.009 mole) of the sodium salt of 2-amino-3-benzoylphenylacetic acid in 25 ml. of dry dimethylformamide was treated with 5.0 g. (0.035 mole) of ethyl iodide. The mixture was stirred two hours at room temperature using a magnetic stirrer. The mixture was diluted with water and the aqueous solution extracted several times with ethyl ether. The combined extracts were washed with water, dried over sodium sulfate and concentrated under vacuum to a yellow solid. The solid was recrystallized from absolute ethanol to give 1.7 gms. (61.0%) of yellow needles which melted at 77°-78° C.

Workup

  1. extractionthe aqueous solution extracted several times with ethyl ether
  2. washThe combined extracts were washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum to a yellow solid
  5. customThe solid was recrystallized from absolute ethanol
  6. customto give 1.7 gms

Sources & evidence

ORD record
ord-ad351c94309449a7bfb3d738e9300aa7
Source dataset
uspto-grants-1977_08
Patent number
US04045576

Reaction notes

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