6-Chloroindoline-2,3-dione → HCID 57803071, compound

HRID 2102723Notes

Reaction equation

HRID 2102723 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][C:7]=1[CH3:8].[Cl:11][C:12]1[CH:20]=[C:19]2[C:15]([C:16](=[O:22])[C:17](=[O:21])[NH:18]2)=[CH:14][CH:13]=1>O1CCCC1>[Cl:11][C:12]1[CH:20]=[C:19]2[C:15]([C:16]([C:4]3[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=3)([OH:22])[C:17](=[O:21])[NH:18]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 2413316-Chloroindoline-2,3-dioneHCID 178426142HCID 178426142, compound

Product 1

HCID 57803071HCID 57803071, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-25 °C

Procedure

A solution of 3,4-dimethylphenyl magnesium bromide in tetrahydrofuran (0.5 M, 3.3 mL, 1.65 mmol) (Aldrich) was added dropwise with magnetic stirring to a suspension of 6-chloroisatin (0.2 g, 1.1 mmol) in tetrahydrofuran (5 mL) with cooling in a −25° C. bath. Cooling bath was then removed and mixture was allowed to warm to room temperature. After stirring for an additional 3 hours, 15% aqueous ammonium chloride solution was added and mixture extracted with ethyl acetate. The combined organic layers were then washed with water, brine, combined, dried (Na2SO4), filtered and concentrated. Residue was stirred in dichloromethane at room temperature for 15 minutes and filtered to give crude rac-6-chloro-3-(3,4-dimethyl-phenyl)-3-hydroxy-1,3-dihydro-indol-2-one as a yellow solid. This was used in the next step without further purification.

Workup

  1. temperatureCooling bath
  2. customwas then removed
  3. temperatureto warm to room temperature
  4. addition15% aqueous ammonium chloride solution was added
  5. extractionmixture extracted with ethyl acetate
  6. washThe combined organic layers were then washed with water, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. stirringResidue was stirred in dichloromethane at room temperature for 15 minutes
  11. filtrationfiltered

Sources & evidence

ORD record
ord-a6259b137aba4b9693dd34741a4566c0
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

Loading…