Acetic Acid → (2-Acetamido-3-benzoylphenyl)acetic acid

HRID 2051863Notes

Reaction equation

HRID 2051863 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]([OH:20])=[O:19].C(O)(=[O:23])C.O=[O+][O-].[OH2:28]>>[C:2]([NH:3][C:4]1[C:9]([C:10](=[O:23])[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]([OH:20])=[O:19])(=[O:28])[CH3:1]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 24823OzoneHCID 20378312(2-Methyl-3-phenyl-1H-indol-7-yl)acetic acid

Product 1

HCID 15634767(2-Acetamido-3-benzoylphenyl)acetic acid

Procedure

A solution of 2 g. of α-(2-methyl-3-phenylindol-7-yl)acetic acid in 60 ml. of acetic acid was treated with ozone for 15 minutes. The reaction mixture was treated with 10 ml. of water and allowed to evaporate overnight. The residue (1.7 g.) was recrystallized from isopropanol; yield 1.6 g. (71%); m.p. 188°-190° C.

Workup

  1. additionThe reaction mixture was treated with 10 ml
  2. customto evaporate overnight
  3. customThe residue (1.7 g.) was recrystallized from isopropanol

Sources & evidence

ORD record
ord-43e3714388b94dd393db0ad627546bd2
Source dataset
uspto-grants-1980_01
Patent number
US04182774

Reaction notes

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