6-Chloroindoline-2,3-dione → HCID 57803055, compound

HRID 2102716Notes

Reaction equation

HRID 2102716 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[Mg]Br.[Cl:13][C:14]1[CH:22]=[C:21]2[C:17]([C:18](=[O:24])[C:19](=[O:23])[NH:20]2)=[CH:16][CH:15]=1>O1CCCC1>[Cl:13][C:14]1[CH:22]=[C:21]2[C:17]([C:18]([OH:24])([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[C:19](=[O:23])[NH:20]2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 2413316-Chloroindoline-2,3-dioneHCID 178418423HCID 178418423, compound

Product 1

HCID 57803055HCID 57803055, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-25 °C

Procedure

A solution of 2-naphthylmagnesium bromide in tetrahydrofuran (0.5 M, 8.26 mL, 4.13 mmol) (Aldrich) was added dropwise with magnetic stirring to a suspension of 6-chloroisatin (0.3 g, 1.67 mmol) in tetrahydrofuran (10 mL) with cooling in a −25° C. bath at such a rate that reaction temperature was kept below −10° C. Cooling bath was then removed and mixture was allowed to warm to room temperature. After stirring for an additional 4 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-naphthalen-2-yl-1,3-dihydro-indol-2-one as a red solid. This was used in the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-8faf8c21bee44d2c9fb9065396dbf9dd
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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