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

HRID 1704316Notes

Reaction equation

HRID 1704316 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-c56a9060aefd4d91ab00c00c819339a8
Source dataset
uspto-grants-1978_11
Patent number
US04126635

Reaction notes

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