Acetic Anhydride → 1H-Indole-2,3-dione, 1-acetyl-5-methyl-

HRID 6359

Reaction equation

HRID 6359 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].[H-].[Na+].[C:15](OC(=O)C)(=[O:17])[CH3:16].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[C:15]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([CH3:1])=[CH:10][CH:9]=2)[C:5](=[O:12])[C:6]1=[O:11])(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 118405-MethylisatinHCID 24758Sodium hydrideHCID 516892Sodium Bicarbonate

Product 1

HCID 5399471H-Indole-2,3-dione, 1-acetyl-5-methyl-Yield 47.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

With stirring at 0° C., 8.06 g (50.0 mmols) of 5-methylisatin was added by small portions to a solution of 2.00 g (50.0 mmols) of sodium hydride in toluene. While stirring under ice cooling, 4.7 ml (50.0 mmols) of acetic anhydride was dropwise added to the mixture followed by heating at 80° C. for further an hour with stirring. After completion of the reaction, an aqueous saturated sodium bicarbonate solution was added to the reaction mixture. The crystals were filtered, washed with water and dried to give 4.84 g (yield, 47%) of 1-acetyl-5-methylisatin.

Workup

  1. stirringWhile stirring under ice cooling
  2. temperatureby heating at 80° C. for further an hour
  3. stirringwith stirring
  4. customAfter completion of the reaction
  5. filtrationThe crystals were filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-b0cbbbccef144c919960c98519e95613
Source dataset
uspto-grants-1993_09
Patent number
US05248684

Linked notes

Loading…