Sodium Iodide → 6-Bromo-4-iodoquinoline

HRID 1096770Notes

Reaction equation

HRID 1096770 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2Cl.[I-:14].[Na+].C(#N)CC.S([O-])([O-])=O.[Na+].[Na+]>C([O-])([O-])=O.[K+].[K+]>[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[I:14]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7854PropionitrileHCID 24437Sodium SulfiteHCID 667822766-Bromo-4-chloroquinoline hydrochloride

Product 1

HCID 177505956-Bromo-4-iodoquinolineYield 100.9%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

A 3-neck roundbottom flask equipped with a reflux condenser and mechanical stirrer was charged with 6-bromo-4-chloroquinoline hydrochloride (34.6 g, 0.124 mol), anhydrous sodium iodide (92.93 g, 0.62 mol) and propionitrile (1 L). The resulting slurry was stirred vigorously at reflux for 96 hrs. The solution was cooled to room temperature and 500 mL of 10% K2CO3 solution was added, followed by a 200 mL of a 5% sodium sulfite solution. The reaction mixture was extracted with CH2Cl2 (600 mL×4). The combined organic extracts were dried (Na2SO4), filtered and conc. in vacuo to provide the title compound as an off-white solid (41.8 g, >quantitative yield), which was used without further purification. LCMS [α]+=333.8, 334.8, 336.0 and 337.0; H1 NMR (400 MHz, d-DMSO) δ (ppm)=7.98-7.96 (2H, m), 8.14-8.16 (1H, m), 8.23 (1H, d), 8.53 (1H, d).

Workup

  1. customA 3-neck roundbottom flask equipped with a reflux condenser and mechanical stirrer
  2. temperatureat reflux for 96 hrs
  3. extractionThe reaction mixture was extracted with CH2Cl2 (600 mL×4)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered and conc. in vacuo

Sources & evidence

ORD record
ord-b1aac089f6644e33a9261771c3d1bf64
Source dataset
uspto-grants-2012_03
Patent number
US08138347B2

Reaction notes

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