Ethanol → 6-Iodoindoline

HRID 907179Notes

Reaction equation

HRID 907179 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) 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.

Workup

  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

Sources & evidence

ORD record
ord-0ec4d54cb95b4cc78d773166451d5bb4
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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