Sodium Iodide → 2-Iodoquinoline

HRID 1895047Notes

Reaction equation

HRID 1895047 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[I-:12].[Na+].C(Cl)(=O)C>CC#N>[I:12][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6367Acetyl chlorideHCID 119282-Chloroquinoline

Product 1

HCID 810442-IodoquinolineYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

2-Iodoquinoline was prepared according to the procedure of Kimber, et. al. (Tetrahedron 2000, 56, 3575). To a solution of 2-chloroquinoline (10.0 g, 61.5 mmol) in CH3CN (100 mL) was added sodium iodide (14 g, 92.3 mmol) and acetyl chloride (8.8 mL, 123 mmol). The reaction mixture was stirred at 100° C. for 5 hours, then cooled to room temperature and quenched with 10% aqueous K2CO3 (100 mL) and 5% aqueous NaHSO3 (50 mL). The aqueous layer was extracted twice with dichloromethane then the combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (0% to 20% EtOAc in hexanes) to provide 9.7 g (70%) of 2-iodoquinoline as a yellow solid.

Workup

  1. custom2-Iodoquinoline was prepared
  2. temperaturecooled to room temperature
  3. customquenched with 10% aqueous K2CO3 (100 mL) and 5% aqueous NaHSO3 (50 mL)
  4. extractionThe aqueous layer was extracted twice with dichloromethane
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (0% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-28a9d9a8e1d449dab8910554ad4c9101
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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