Ethanol → 1-(4-Acetoxybenzyl)indoline-2,3-dione

HRID 851764Notes

Reaction equation

HRID 851764 reaction equation
C(O)C.[OH-].[K+].[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[C:7]1=[O:16].[C:17]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1)(=[O:19])[CH3:18]>CS(C)=O>[C:17]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:15])[C:7]2=[O:16])=[CH:23][CH:22]=1)(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 7054IsatinHCID 14797Potassium HydroxideHCID 109987714-(Bromomethyl)phenyl acetate

Product 1

HCID 204340301-(4-Acetoxybenzyl)indoline-2,3-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

An ethanol solution of potassium hydroxide (16.6 g. in 400 ml.) was added to a stirred solution of indoline-2,3-dione (isatin) (43.6 g.) in dimethyl sulphoxide (400 ml.). After 10 minutes a solution of 4-acetoxybenzyl bromide (76.3 g.) in dimethyl sulphoxide (40 ml.) was added. The mixture was stirred for 72 hours and then poured into ice/water (~1000 ml.). The gum which first formed slowly crystallised. The solid which formed was recrystallised from methanol (500 ml.) to give 1-(4-acetoxybenzyl)indoline-2,3-dione as a solid, m.p. 159°-161° C.

Workup

  1. customThe gum which first formed slowly
  2. customcrystallised
  3. customThe solid which formed
  4. customwas recrystallised from methanol (500 ml.)

Sources & evidence

ORD record
ord-dab6fbac1b5f423a9598a761fb08df94
Source dataset
uspto-grants-1983_05
Patent number
US04386100

Reaction notes

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