Sodium Iodide → 6-Iodoquinoline

HRID 1661809Notes

Reaction equation

HRID 1661809 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-Iodoquinoline

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 chromatographied over silica gel with CH2Cl2 100% and CH2Cl2/MeOH:95/5 to yield 3.56 g (97%) of 6-Todoquinoline as a light yellow solid.

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. custom95/5 to yield 3.56 g (97%) of 6-Todoquinoline as a light yellow solid

Sources & evidence

ORD record
ord-a81b7a1e5c0649e7ad4cf6eac8edb27e
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

Loading…