Water → 6-Iodoquinoline

HRID 469188Notes

Reaction equation

HRID 469188 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[I-:12].[Na+].[I-].O>C(O)CCC.[Cu]>[I:12][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 30165Iodide IonHCID 792436-Bromoquinoline

Product 1

HCID 203985536-IodoquinolineYield 80%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalyst2×HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

6-bromoquinoline (80.1 g, 0.385 mol) is dissolved in n-butanol (0.8 L). Copper catalyst CuI (3.7 g, 0.019 mol), a copper-ligand N,N′-dimethylethylenediamine (3.4 g, 0.0385 mol) and an iodide source NaI (115.5 g, 0.770 mol) are added and the mixture is heated in a heating jacket, under inert atmosphere to 120° C. After work-up (0.8 L water is added to the reaction mixture, the organic layer is separated off and evaporated) and purification (the crude evaporation residue was crystallized from 150 mL diisopropylether), 6-iodoquinoline was obtained in 80% yield.

Workup

  1. customthe organic layer is separated off
  2. customevaporated) and
  3. custompurification (the crude
  4. customevaporation residue
  5. customwas crystallized from 150 mL diisopropylether), 6-iodoquinoline
  6. customwas obtained in 80% yield

Sources & evidence

ORD record
ord-d0b1883730fe4c7eafa57729e9a888eb
Source dataset
uspto-grants-2014_01
Patent number
US08629144B2

Reaction notes

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