Potassium Iodide → 6-Iodoisoquinoline

HRID 751309Notes

Reaction equation

HRID 751309 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.[I-:12].[K+].ClCCl.C(OCC)C>CN(C)C=O.[Cu]I>[I:12][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 3136816-BromoisoquinolineHCID 21881112Ethyl ether methylene chloride

Product 1

HCID 126795216-IodoisoquinolineYield 101.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

Heat a mixture of 6-bromoisoquinoline (Aldrich; 0.320 g, 1.54 mmol), copper (I) iodide (0.155 g, 0.815 mmol), and potassium iodide (1.27 g, 7.96 mmol) in N,N-dimethylformamide (5.0 mL) to 130° C. at 3 h under microwave irradiation. Pour the cooled reaction mixture into 4:1 dichloromethane/diethyl ether (100 mL) and filter. Wash the filtrate with 5% aqueous sodium bisulfite solution (2×50 mL). Dry the organic layer over sodium chloride, decant the organic layer, and remove the solvents under reduced pressure. Dry the residue under vacuum for 18 h to give 0.4 g (100%) of the title compound as a dark red-brown solid. This material is carried on directly to the next step without further purification. MS (electrospray, m/z) 256.1 (M+1).

Workup

  1. temperatureHeat
  2. customunder microwave irradiation
  3. additionPour
  4. filtrationfilter
  5. washWash the filtrate with 5% aqueous sodium bisulfite solution (2×50 mL)
  6. dry with materialDry the organic layer over sodium chloride
  7. customdecant the organic layer
  8. customremove the solvents under reduced pressure
  9. customDry the residue under vacuum for 18 h

Sources & evidence

ORD record
ord-ed644dd13a6048318f45f6cc8449813c
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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