Acetic Anhydride → HCID 13957978, compound

HRID 580328Notes

Reaction equation

HRID 580328 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:18])=[O:8])[CH:2]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>>[C:19]([N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]([C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[O:8])[C:10]1=[O:18])(=[O:21])[CH3:20]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 13958012HCID 13958012, compound

Product 1

HCID 13957978HCID 13957978, compound

Procedure

A mixture of 476 mg (2.0 mmole) of 3-(3-pyridylcarbonyl)-2-oxindole and 4 ml of acetic anhydride was heated under reflux for 30 minutes. The reaction mixture was cooled to room temperature, the bulk of the acetic anhydride was removed by evaporation in vacuo and the residue was triturated under 15 ml of water. The solid was recovered by filtration, dried and triturated under isopropanol. The residue (158 mg) was recrystallized from acetonitrile giving 64 mg of the title compound as red-orange crystals, m.p. 142.5°-143.5° C. A second crop of title compound (40 mg) was obtained from the mother liquors from the recrystallization. The two crops were the same by thin-layer chromatography. The first crop was subjected to elemental analysis.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. customthe bulk of the acetic anhydride was removed by evaporation in vacuo
  4. customthe residue was triturated under 15 ml of water
  5. filtrationThe solid was recovered by filtration
  6. customdried
  7. customtriturated under isopropanol
  8. customThe residue (158 mg) was recrystallized from acetonitrile giving 64 mg of the title compound as red-orange crystals, m.p. 142.5°-143.5° C

Sources & evidence

ORD record
ord-a3f3cbf6da274eecb9c3955e22beef1f
Source dataset
uspto-grants-1988_06
Patent number
US04752609

Reaction notes

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