Methanol → 6-Chloroindoline-2,3-dione

HRID 853852Notes

Reaction equation

HRID 853852 reaction equation
Br[C:2]1(Br)[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12].C[OH:15]>O>[Cl:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2](=[O:15])[C:3](=[O:12])[NH:4]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 12032310HCID 12032310, compound

Product 1

HCID 2413316-Chloroindoline-2,3-dioneYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,3-Dibromo-6-chloro-1,3-dihydro-indol-2-one (21.34 g, 59.7 mmol) was suspended in a 4:1 (v:v) mixture of MeOH (172 mL): water (43 mL) and heated at reflux for 19 hr. The reaction was cooled in an ice bath and filtered. The red solid was washed once with cold CH3OH and dried to give the title compound as a red solid (10.49 g, 88% yield). NMR (400 MHz, DMSO-d6): consistent. MS: (API-ES+) m/z 182/184 [M+H], 1 chlorine pattern observed.

Workup

  1. temperatureat reflux for 19 hr
  2. temperatureThe reaction was cooled in an ice bath
  3. filtrationfiltered
  4. washThe red solid was washed once with cold CH3OH
  5. customdried

Sources & evidence

ORD record
ord-ba6099e14c3847be8aa9f7c26935e726
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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