5-Methylisatin → 7-Bromo-5-methylindoline-2,3-dione

HRID 868567Notes

Reaction equation

HRID 868567 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].[Br:13]Br>C(O)(=O)C>[Br:13][C:9]1[CH:10]=[C:2]([CH3:1])[CH:3]=[C:4]2[C:8]=1[NH:7][C:6](=[O:11])[C:5]2=[O:12]

Participants

4

Reactant 2

HCID 118405-MethylisatinHCID 24408Bromine

Product 1

HCID 6116217-Bromo-5-methylindoline-2,3-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a suspension of 8.0 g of 5-methylisatin in 200 ml of acetic acid was added dropwise a solution of 3.3 ml of bromine in 50 ml of acetic acid with stirring at room temperature, and the mixture was heated at 50° C. for 16 hours. The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized from methanol-hexane to obtain 11.4 g of 7-bromo-5-methylisatin having a melting point of 176°-180° C.

Workup

  1. temperaturethe mixture was heated at 50° C. for 16 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was recrystallized from methanol-hexane

Sources & evidence

ORD record
ord-e464e95d98324dbe8b7ef8efaf54000c
Source dataset
uspto-grants-1988_10
Patent number
US04780477

Reaction notes

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