Acetic Anhydride → N-(2-oxoindolin-5-yl)acetamide

HRID 1387418Notes

Reaction equation

HRID 1387418 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[C:12](OC(=O)C)(=[O:14])[CH3:13]>>[O:11]=[C:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:12](=[O:14])[CH3:13])[CH:3]=2)[NH:7]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 27732135-Amino-2-oxindole

Product 1

HCID 11206280N-(2-oxoindolin-5-yl)acetamideYield 46%

Procedure

A mixture of 200 mg (1.35 mmol) of 5-amino 1,3-dihydro-indol-2-one in 6 ml of acetic anhydride was refluxed for 30 minutes. The reaction mixture was poured onto 50 g of crushed ice. The mixture was stirred well and the solid was collected by vacuum filtration. The solid was washed with 200 ml of H2O and air dried to yield N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (119 mg, 46%): 1H NMR (DMSO-d6): δ1.97 (s, 3H), 3.41 (s, 2H), 6.68 (d, J=8.4 Hz, 1H), ), 7.26 (dd, J1=2 Hz, J2=8.4 Hz, 1H), 7.46 (d, J=2 Hz, 1H), 9.73 (s, 1H). 10.23 (s, 1H),

Workup

  1. temperaturewas refluxed for 30 minutes
  2. filtrationthe solid was collected by vacuum filtration
  3. washThe solid was washed with 200 ml of H2O and air
  4. customdried

Sources & evidence

ORD record
ord-5d94eafbc44046cea6402f436a9cd005
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

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