Sodium Iodide → 6-Iodoquinoline

HRID 1959645Notes

Reaction equation

HRID 1959645 reaction equation
[I-:1].[Na+].Br[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2>[Cu]I.O1CCOCC1>[I:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 792436-Bromoquinoline

Product 1

HCID 203985536-IodoquinolineYield 95.3%

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), 6-bromo-quinoline (3 g, 14.4 mmol), N,N′-dimethyl-cyclohexane (0.227 mL, 1.44 mmol) and dioxane were charged in a microwave tube (25 mL). The tube was purged with nitrogen for 10 min and sealed with a Teflon septum. The reaction mixture was stirred at 110° C. for 15 h. After cooling, the mixture was poured onto ice-water and extracted with DCM. The crude was purified by silica gel column to give 6-iodo-quinoline as light green solid (3.5 g, 92%).

Workup

  1. customThe tube was purged with nitrogen for 10 min
  2. customsealed with a Teflon septum
  3. temperatureAfter cooling
  4. additionthe mixture was poured onto ice-water
  5. extractionextracted with DCM
  6. customThe crude was purified by silica gel column

Sources & evidence

ORD record
ord-a24fbf879c164055873e84a3bd8f96e0
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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