Ethanol → 6-Iodoindoline

HRID 907179

Reaktionsgleichung

Reaktionsgleichung von HRID 907179
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) were heated at 90° C. overnight. The reaction mixture was then partitioned between H2O and EtOAc. The organic layer was extracted into aqueous HCl. The aqueous layer was in turn basified with NaOH, and was extracted with EtOAc. The organic layer was dried and concentrated. Hexane trituration yielded 6-iodoindoline (577 mg, 64%) as a brown solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-0ec4d54cb95b4cc78d773166451d5bb4
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013006B2

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