Water → 3-Iodoquinoline

HRID 1519822Notes

Reaction equation

HRID 1519822 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.CNCCNC.[I-:18].[Na+].O>O1CCOCC1>[I:18][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 214133-Bromoquinoline

Product 1

HCID 112538363-IodoquinolineYield 87.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Bromoquinoline (64.00 g, 308 mmol), N,N′-dimethylethylenediamine (13.5 ml, 127 mmol), cuprous iodide (12.00 g, 63.0 mmol) and sodium iodide (112 g, 747 mmol) in dioxane (300 ml) was placed into a preheated oil bath at 100° C. After stirring for 18 h, the heterogeneous mixture was diluted water and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was flash chromatographed with methylene chloride as the eluant to afford 68.47 g (87% yield) of 3-iodoquinoline as a yellow solid. Method [8] retention time 6.47 min by HPLC (M+=256).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed with methylene chloride as the eluant

Sources & evidence

ORD record
ord-b52b18b600f44dfd9744ddd27494da06
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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