Acetic Anhydride → HCID 13958009, compound

HRID 2308717Notes

Reaction equation

HRID 2308717 reaction equation
[Cl: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]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:12](=[O:14])[CH3:13])[C:6](=[O:11])[CH2:5]2

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 1528015-Chlorooxindole

Product 1

HCID 13958009HCID 13958009, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7.0 g (42 mmole) of 5-chloro-2-oxindole and 5.9 ml (63 mmole) of acetic anhydride was heated under nitrogen at reflux for 3.5 hours. The cooled reaction mixture was diluted with 300 ml of ethyl acetate, and the resulting solution was washed with aqueous sodium bicarbonate followed by saturated, aqueous sodium chloride solution. The ethyl acetate solution was then dried (Na2SO4) and evaporated in vacuo to give 8.3 g of a purple solid. The latter solid was purified by chromatography on silica gel, eluting with 2.5% ethyl acetate in dichloromethane, to give 6.0 g of crude title compound as a yellow solid. The latter solid was recrystallized from ca. 50 ml of ethanol to give 4.7 g of the title compound as pale yellow needles, m.p. 129°-130° C.

Workup

  1. temperaturewas heated under nitrogen
  2. temperatureat reflux for 3.5 hours
  3. customThe cooled reaction mixture
  4. washthe resulting solution was washed with aqueous sodium bicarbonate
  5. dry with materialThe ethyl acetate solution was then dried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-868fa23c2fd6452e88e9477d24c46568
Source dataset
uspto-grants-1987_09
Patent number
US04690943

Reaction notes

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