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Potassium Iodide → (+/-)-Ethyl methyl 2,2'-(4-nitro-2,3-dihydro-1H-indole-1,3-diyl)diacetate

HRID 2353301
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2353301
C[CH:2]([CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[N+:15]([O-:17])=[O:16])[NH:8][CH2:7]1)[C:3]([O-:5])=[O:4].[C:18](=O)(O)[O-].[Na+].[I-].[K+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>CC(C)=O>[N+:15]([C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[CH:6]([CH2:2][C:3]([O:5][CH3:18])=[O:4])[CH2:7][N:8]2[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])([O-:17])=[O:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 516892Sodium BicarbonateHCID 66636769HCID 66636769, Verbindung

Produkt 1

HCID 59257866(+/-)-Ethyl methyl 2,2'-(4-nitro-2,3-dihydro-1H-indole-1,3-diyl)diacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180
Acetone
Lösungsmittel

Versuchsvorschrift

To a solution of (±)-methyl(4-nitro-2,3-dihydro-1H-indol-3-yl)acetate from Step B (700 mg, 3.0 mmol), sodium bicarbonate (471 mg, 4.4 mmol), and potassium iodide (98 mg, 0.59 mmol) in acetone (15 mL) was added ethyl bromoacetate (9.9 mL, 88.9 mmol). The mixture was heated at reflux for 18 h, then cooled to ambient temperature and concentrated in vacuo. The residue was partitioned between H2O (15 mL) and EtOAc (2×40 mL) and the organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to a volume of 50 mL. Hexane was added to the EtOAc solution and a precipitate formed. The desired crystals were collected by vacuum filtration to give the title compound. MS: m/z 323 (M+1).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between H2O (15 mL) and EtOAc (2×40 mL)
  5. washthe organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to a volume of 50 mL
  9. additionHexane was added to the EtOAc solution
  10. customa precipitate formed
  11. filtrationThe desired crystals were collected by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-f2f152554ac74899a9d5399d5f4a1a0d
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07750010B2

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