Acetic Acid → Ethyl (2-acetamido-3-benzoylphenyl)acetate

HRID 2051862Notes

Reaction equation

HRID 2051862 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(O)(=[O:25])C.O=[O+][O-].[OH2:30]>>[C:2]([NH:3][C:4]1[C:9]([C:10](=[O:25])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])(=[O:30])[CH3:1]

Participants

5

Reactant 4

HCID 176Acetic Acid2×HCID 962WaterHCID 24823OzoneHCID 23342680Ethyl (2-methyl-3-phenyl-1H-indol-7-yl)acetate

Product 1

HCID 54304647Ethyl (2-acetamido-3-benzoylphenyl)acetate

Procedure

A solution of 5 g. (0.017 mole) of ethyl α-(2-methyl-3-phenylindol-7-yl)acetate and 75 ml. of acetic acid was treated with ozone for 25 minutes. After ozonation, the acetic acid solution was diluted with water and extracted with ether. The ether extracts were washed with water, 5% sodium carbonate, dried (magnesium sulfate) and concentrated. Recrystallization from isopropanol gave 2.6 g. (47%) of product which melted at 133°-134° C.

Workup

  1. extractionextracted with ether
  2. washThe ether extracts were washed with water, 5% sodium carbonate
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customRecrystallization from isopropanol
  6. customgave 2.6 g

Sources & evidence

ORD record
ord-e41521fd0c30499ca37edd637820198d
Source dataset
uspto-grants-1980_01
Patent number
US04182774

Reaction notes

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