Iodine → 3-(2-Ethoxy-phenyl)-3-hydroxy-5-methoxy-1,3-dihydro-indol-2-one

HRID 2040437Notes

Reaction equation

HRID 2040437 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:10][CH3:11].II.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[C:19]2=[O:26]>C(OCC)C.C1COCC1>[CH2:10]([O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:19]1([OH:26])[C:18]2[C:22](=[CH:23][CH:24]=[C:16]([O:15][CH3:14])[CH:17]=2)[NH:21][C:20]1=[O:25])[CH3:11]

Participants

7

Reactant 4

HCID 807IodineHCID 383335-MethoxyisatinHCID 685002-Bromophenetole2×HCID 5462224Magnesium

Product 1

HCID 575177763-(2-Ethoxy-phenyl)-3-hydroxy-5-methoxy-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

40 g (1.65 mol) of magnesium chips and 5% of the total amount of the 2-bromo-1-ethoxy benzene were added to 100 ml diethyl ether and after adding a few crystals iodine the mixture was carefully heated to initiate the reaction. To the refluxing mixture the remaining amount of 203 ml (1.65 mol) 2-bromo-1-ethoxy benzene, dissolved in 450 ml diethyl ether, was added slowly to maintain the reaction. Then 75 g (0.41 mol) of 5-methoxyisatine, suspended in 750 ml THF, were added to the cooled reaction mixture. After stirring the reaction mixture for 30 minutes at ambient temperature, the mixture was poured into an ice/aqueous NH4Cl mixture. The aqueous phase was extracted with ethyl acetate several times and the combined organic phase was washed with H2O, dried over magnesium sulfate and the solvent was removed in vacuo.

Workup

  1. temperaturewas carefully heated
  2. customthe reaction
  3. additionwas added slowly
  4. temperatureto maintain
  5. customthe reaction
  6. additionwere added to the cooled reaction mixture
  7. extractionThe aqueous phase was extracted with ethyl acetate several times
  8. washthe combined organic phase was washed with H2O
  9. dry with materialdried over magnesium sulfate
  10. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d72332ec986c47a0852ce063c333fd35
Source dataset
uspto-grants-2013_11
Patent number
US08580842B2

Reaction notes

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