6-Chloroindoline-2,3-dione → HCID 57803086, compound

HRID 2102666Notes

Reaction equation

HRID 2102666 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][CH:8]=1.[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]([OH:22])([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:17](=[O:21])[NH:18]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 2413316-Chloroindoline-2,3-dioneHCID 178490745HCID 178490745, compound

Product 1

HCID 57803086HCID 57803086, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-25 °C

Procedure

A solution of 3-methoxyphenyl magnesium bromide in tetrahydrofuran (1.0 M, 25 mL, 25 mmol) (Aldrich) was added dropwise with magnetic stirring to a suspension of 6-chloroisatin (1.82 g, 10 mmol) in tetrahydrofuran (40 mL) under argon with cooling in a −25° C. bath at such a rate that reaction temperature was kept below −10° C. (approximately 30 minutes). Cooling bath was then removed and mixture allowed to warm to room temperature. After stirring for an additional 2 hour, 15% aqueous ammonium chloride solution (25 mL) and water (50 mL) were added and mixture extracted with ethyl acetate (2×75 mL). Ethyl acetate layers were then washed with water (75 mL), brine (75 mL), combined, dried (MgSO4), filtered and concentrated. Residue was stirred in dichloromethane (100 mL) at room temperature for 15 minutes and filtered to give crude rac-6-chloro-3-hydroxy-3-(3-methoxy-phenyl)-1,3-dihydro-indol-2-one as an off-white powder. This was used in the next step without further purification.

Workup

  1. customthat reaction temperature
  2. customwas kept below −10° C.
  3. custom(approximately 30 minutes)
  4. temperatureCooling bath
  5. customwas then removed
  6. temperatureto warm to room temperature
  7. addition15% aqueous ammonium chloride solution (25 mL) and water (50 mL) were added
  8. extractionmixture extracted with ethyl acetate (2×75 mL)
  9. washEthyl acetate layers were then washed with water (75 mL), brine (75 mL)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. stirringResidue was stirred in dichloromethane (100 mL) at room temperature for 15 minutes
  14. filtrationfiltered

Sources & evidence

ORD record
ord-43364b62a034438db52eac1827a6fb1e
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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