Sodium hydride → 3-(2,4-dimethoxyphenyl)-3-hydroxy-5,6-dimethoxy-1,3-dihydro-2H-indol-2-one

HRID 490140

Reaktionsgleichung

Reaktionsgleichung von HRID 490140
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[NH:10][C:9](=[O:16])[C:8]2=[O:17].[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1Br.[Mg].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[C:8]1([OH:17])[C:7]2[C:11](=[CH:12][C:13]([O:14][CH3:15])=[C:5]([O:4][CH3:3])[CH:6]=2)[NH:10][C:9]1=[O:16]

Komponenten

8

Edukt 5

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 872661-Bromo-2,4-dimethoxybenzeneHCID 47391485,6-dimethoxy-2,3-dihydro-1H-indole-2,3-dioneHCID 5462224Magnesium

Produkt 1

HCID 231206493-(2,4-dimethoxyphenyl)-3-hydroxy-5,6-dimethoxy-1,3-dihydro-2H-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

293 mg of 60% sodium hydride was added under ice cooling and a nitrogen gas flow to a suspension of 1.38 g of 5,6-dimethoxy-1H-indol-2,3-dione in 30 mL of tetrahydrofuran, and the reaction mixture was stirred for 1 hour at the same temperature. A Grignard's reagent generated in 20 mL of tetrahydrofuran using 3.61 g of 2,4-dimethoxybromobenzene and 486 mg of magnesium was added dropwise over a period of 3 minutes to the reaction mixture under ice cooling, after which the reaction mixture was stirred for 13 hours at room temperature. 20 mL of saturated aqueous ammonium chloride and 40 mL of ethyl acetate were added to the reaction solution, and the reaction mixture was stirred for 30 minutes at room temperature. After liquid separation, the aqueous layer was extracted with ethyl acetate (20 mL×2), the combined organic layer was washed with saturated brine and dried with magnesium sulfate, and the drying agent was then filtered off and the filtrate was concentrated under reduced pressure. The residue thus obtained was purified by column chromatography (silica gel 60, mobile phase: ethyl acetate) to obtain 1.37 g of the titled compound (brown solid).

Aufarbeitung

  1. additionwas added dropwise over a period of 3 minutes to the reaction mixture under ice cooling
  2. stirringafter which the reaction mixture was stirred for 13 hours at room temperature
  3. stirringthe reaction mixture was stirred for 30 minutes at room temperature
  4. customAfter liquid separation
  5. extractionthe aqueous layer was extracted with ethyl acetate (20 mL×2)
  6. washthe combined organic layer was washed with saturated brine
  7. dry with materialdried with magnesium sulfate
  8. filtrationthe drying agent was then filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by column chromatography (silica gel 60, mobile phase: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3a43af50ad7e46c7a423c350c34aa9be
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528124B2

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