Sodium Iodide → 6-Iodoquinoline

HRID 1921633Notes

Reaction equation

HRID 1921633 reaction equation
[I-:1].[Na+].CNC1CCCCC1NC.Br[C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][CH:18]=[CH:17]2>O1CCOCC1.[Cu]I>[I:1][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][CH:18]=[CH:17]2

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 792436-BromoquinolineHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamine

Product 1

HCID 203985536-IodoquinolineYield 97%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Sodium iodide (4.32 g, 28.8 mmol), Copper (I) iodide (137 mg, 0.72 mmol) and N,N′-Dimethyl-cyclohexane-1,2-diamine (0.227 mL, 1.44 mmol) and 6-Bromoquinoline (3 g, 14.4 mmol) in dioxane (15 mL) were charged in a 25 mL microwave tube. The tube was flushed with Nitrogen and sealed with a Teflon septum and Nitrogen was bubbled in the solution for 10 minutes, allowing the gas to escape through a needle. After the removal of the needle, the reaction mixture was stirred at 110° C. for 15 hours. Then, the green suspension was allowed to reach room temperature, poured into ice-water and extracted with dichloromethane. The organic layer was collected, dried (MgSO4), filtered and concentrated in vacuum. The crude mixture was chromatographed over silica gel with CH2Cl2 100% and CH2Cl2/MeOH:95/5 to yield 3.56 g (97%) of 6-Iodoquinoline as a light yellow solid. 1H-NMR (DMSO): δ 8.93 (1H, dd, J=1.5, 4.1 Hz), 8.47 (1H, d, J=2.0 Hz), 8.33 (1H, d, J=8.6 Hz), 8.02 (1H, dd, J=2.0, 8.6 Hz), 7.80 (1H, d, J=8.6 Hz), 7.56 (1H, dd, J=4.1, 8.6 Hz).

Workup

  1. customThe tube was flushed with Nitrogen
  2. customsealed with a Teflon septum and Nitrogen
  3. customwas bubbled in the solution for 10 minutes
  4. customAfter the removal of the needle
  5. customto reach room temperature
  6. additionpoured into ice-water
  7. extractionextracted with dichloromethane
  8. customThe organic layer was collected
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuum
  12. customThe crude mixture was chromatographed over silica gel with CH2Cl2 100% and CH2Cl2/MeOH

Sources & evidence

ORD record
ord-a8281fc4721b41c38aa5dfcdd29cfcd4
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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