Ethanol → 6-Iodoindoline

HRID 506079Notes

Reaction equation

HRID 506079 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 116156966-IodoindolineYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b285cc92f2814a68946c85edd40a9ab3
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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