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

HRID 1704329Notes

Reaction equation

HRID 1704329 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-a7f67a3877ab49fcb90ee4e12821fa23
Source dataset
uspto-grants-1978_11
Patent number
US04126635

Reaction notes

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