Sodium Iodide → 3-Benzyl-7-chloro-2 iodo-quinoline

HRID 271830Notes

Reaction equation

HRID 271830 reaction equation
[CH2:1]([C:8]1[C:9](Cl)=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([Cl:18])[CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:20].[Na+].I>C(C(C)=O)C>[CH2:1]([C:8]1[C:9]([I:20])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([Cl:18])[CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 24841Hydrogen iodideHCID 59836190HCID 59836190, compound

Product 1

HCID 598361993-Benzyl-7-chloro-2 iodo-quinolineYield 99%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-benzyl-2,7-dichloroquinoline (3.0 g, 10.4 mmol) and sodium iodide (15.6 g, 104 mmol) in 30 mL of methyl ethyl ketone was heated to 80° C. To this was added hydroiodic acid (1.13 ml, 13.2 mmol). The reaction mixture was heated at 80° C. for 1.5 hours and then cooled to ambient temperature. The reaction was quenched with H2O. Excess ethyl acetate was added to the reaction mixture and the organic layer was washed with saturated NaHCO3, saturated Na2S2O3, brine, dried over MgSO4, filtered and the solvent was removed in vacuo to yield 3.9 g (10.3 mmol, 99%) of 3-benzyl-7-chloro-2 iodo-quinoline 23 as a tan solid.

Workup

  1. temperatureThe reaction mixture was heated at 80° C. for 1.5 hours
  2. temperaturecooled to ambient temperature
  3. customThe reaction was quenched with H2O
  4. additionExcess ethyl acetate was added to the reaction mixture
  5. washthe organic layer was washed with saturated NaHCO3, saturated Na2S2O3, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cb87a0e1cd834c278f4f853ec235ce46
Source dataset
uspto-grants-2008_11
Patent number
US07452996B2

Reaction notes

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