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

HRID 442533Notes

Reaction equation

HRID 442533 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-7yl)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-f6ae27a9a5f04c889ad023b7cf9e42af
Source dataset
uspto-grants-1977_08
Patent number
US04045576

Reaction notes

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