5-Iodoisatin → 3-Hydroxy-5-iodo-3-phenyl-1,3-dihydro-indol-2-one

HRID 513247Notes

Reaction equation

HRID 513247 reaction equation
CO[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Mg]Br.[I:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2=[O:22]>CCOCC.C1COCC1>[OH:22][C:15]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:14]2[C:18](=[CH:19][CH:20]=[C:12]([I:11])[CH:13]=2)[NH:17][C:16]1=[O:21]

Participants

5

Reactant 2

HCID 886955-IodoisatinHCID 178489560HCID 178489560, compound

Product 1

HCID 1175996703-Hydroxy-5-iodo-3-phenyl-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3M 2-methoxyphenylmagnesium bromide (0.92 mL, 2.747 mmol) in Et2O is added drop wise to a suspension of 5-iodoisatin (300 mg, 1.099 mmol) in THF whilst cooling in ice. The mixture is then stirred at room temperature for 1 hour. The reaction mixture is quenched by adding ammonium chloride solution and extracted several times with ethyl acetate. The combined organic phases are washed several times with water, dried over MgSO4 and concentrated under reduced pressure. The precipitate is filtered off with suction, washed with very small amounts of ethyl acetate and dried. This afforded the desired product as a light yellow solid.

Workup

  1. temperaturewhilst cooling in ice
  2. customThe reaction mixture is quenched
  3. additionby adding ammonium chloride solution
  4. extractionextracted several times with ethyl acetate
  5. washThe combined organic phases are washed several times with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. filtrationThe precipitate is filtered off with suction
  9. washwashed with very small amounts of ethyl acetate
  10. customdried

Sources & evidence

ORD record
ord-2bb7e4d831be4e1ea0c9ebc7b380580b
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

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