Diethyl Ether → 1-(3,5-Dichlorophenyl)-1,3-dihydro-indol-2-one

HRID 2227795Notes

Reaction equation

HRID 2227795 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClN1C(=[O:24])CCC1=O.CCOCC>C(O)(=O)C.P(=O)(O)(O)O.O>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C:10]2=[O:24])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 31398ChlorosuccinimideHCID 184748081-(3,5-Dichlorophenyl)-1H-indole

Product 1

HCID 184748111-(3,5-Dichlorophenyl)-1,3-dihydro-indol-2-oneYield 71%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 1004Phosphoric AcidSolvent

Procedure

To a solution of 7.8 g (29.9 mmol) of 1-(3,5-Dichlorophenyl)-1H-indole in 50 mL of acetic acid was added 4.0 g (30.1 mmol) of N-chlorosuccinimide. The mixture was warmed at reflux for 1hr, when TLC indicated the disappearance of starting material. The mixture was cooled and diluted with 16 mL of 70% aqueous phosphoric acid and 4 mL of water and warmed at reflux for 6 hr. The reaction was then cooled to afford a precipitate which was diluted with 50 mL of water and collected by filtration. The solid was partially dried by pulling vacuum through the filter cake and then dissolved in dichloromethane, dried (MgSO4), treated with carbon (Norit A), filtered through diatomaceous earth and concentrated to afford an orange solid. Trituration with ether gave 5.9 g (71%) of 1-(3,5-dichlorophenyl)-1,3-dihydro-indol-2-one which was used without further purification.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureat reflux for 1hr
  3. temperatureThe mixture was cooled
  4. temperaturewarmed
  5. temperatureat reflux for 6 hr
  6. temperatureThe reaction was then cooled
  7. customto afford a precipitate which
  8. filtrationcollected by filtration
  9. customThe solid was partially dried
  10. dissolutiondissolved in dichloromethane
  11. dry with materialdried (MgSO4)
  12. additiontreated with carbon (Norit A),
  13. filtrationfiltered through diatomaceous earth
  14. concentrationconcentrated
  15. customto afford an orange solid

Sources & evidence

ORD record
ord-18ee8d4217ce416cafbbbc762f076cd1
Source dataset
uspto-grants-2002_07
Patent number
US06414153B1

Reaction notes

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