Ethanol → 6-Iodoindoline

HRID 1009609

Reaktionsgleichung

Reaktionsgleichung von HRID 1009609
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([I:13])[CH:11]=2)[CH2:6][CH2:5]1)(=O)C.[OH-].[Na+].CCO>O>[I:13][C:10]1[CH:11]=[C:12]2[C:7]([CH2:6][CH2:5][NH:4]2)=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 116663961-Acetyl-6-iodoindoline

Produkt 1

HCID 116156966-IodoindolineAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1-Acetyl-6-iodoindoline (1.06 g, 3.7 mmol), NaOH (1.16 g, 29 mmol), EtOH (8 mL), and H2O (6 mL) are heated at 90° C. overnight. The reaction mixture is then partitioned between H2O and EtOAc. The organic layer is extracted into aqueous HCl. The aqueous layer is in turn basified with NaOH, and is extracted with EtOAc. The organic layer is dried and concentrated. Hexane trituration yields 6-iodoindoline (577 mg, 64%) as a brown solid.

Aufarbeitung

  1. customThe reaction mixture is then partitioned between H2O and EtOAc
  2. extractionThe organic layer is extracted into aqueous HCl
  3. extractionis extracted with EtOAc
  4. customThe organic layer is dried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-39c37c3b0c3d45a8b01105da888629fe
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973069B2

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