Ethanol → 6-Iodoindoline

HRID 252571

Reaktionsgleichung

Reaktionsgleichung von HRID 252571
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-a0f13259a14d43c5b16fbd2049ae4af8
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868037B2

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