6-Chloroindoline-2,3-dione → HCID 57803038, compound

HRID 2102726Notes

Reaction equation

HRID 2102726 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([Mg]Br)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17](=[O:23])[C:18](=[O:22])[NH:19]2)=[CH:15][CH:14]=1>O1CCCC1>[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17]([OH:23])([C:7]3[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=3)[C:18](=[O:22])[NH:19]2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 2413316-Chloroindoline-2,3-dioneHCID 178439193HCID 178439193, compound

Product 1

HCID 57803038HCID 57803038, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-25 °C

Procedure

A solution of 4-isopropyl-phenyl 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-hydroxy-3-(4-isopropyl-phenyl)-1,3-dihydro-indol-2-one as a pale 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-e64b0ab42d2e4fcead87b0e909fb0fde
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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