Amfenac → Methyl 2-amino-3-benzoylphenylacetate

HRID 442548Notes

Reaction equation

HRID 442548 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].[CH3:21]N(C)C=O.CI>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][CH3:21])=[O:19]

Participants

6

Reactant 4

HCID 2136AmfenacHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 5360545Sodium

Product 1

HCID 12901250Methyl 2-amino-3-benzoylphenylacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4.0 g. (0.014 mole) of the sodium salt of 2-amino-3-benzoylphenylacetic acid in 100 ml. of dry dimethylformamide was treated with 8.0 g. (0.057 mole) of methyl iodide. After stirring for two hours the solution was poured into 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 oil. The oil was crystallized from a chilled methanol-water solution to give 3.5 gms. (90%) of a yellow solid which melted at 52°-54° 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 oil
  5. customThe oil was crystallized from a chilled methanol-water solution
  6. customto give 3.5 gms

Sources & evidence

ORD record
ord-162a90665fd24baaab40c7f89201c54b
Source dataset
uspto-grants-1977_08
Patent number
US04045576

Reaction notes

Loading…