Sodium Iodide → 6-Iodopyridine-3-carboxylic acid

HRID 1376799Notes

Reaction equation

HRID 1376799 reaction equation
[I-:1].[Na+].I.Cl[C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][N:6]=1>CC(C)=O>[I:1][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 5238Sodium Iodide2×HCID 24841Hydrogen iodideHCID 792226-Chloronicotinic acid

Product 1

HCID 8190626-Iodopyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 15.962 g ((0.106 mol) of sodium iodide in 51 g (30 ml, 40 mmol) of hydriodic acid were stirred for 5 minutes. To the mixture was added 17.184 g (0.109 mol) of 6-chloro-nicotinic acid and the resulting mixture refluxed at 100°-130 C.°C. for 40 hours. The dark brown mixture was then taken up in 300 ml of acetone and stirred to dissolve the excess NaI. The product was collected by suction filtration, rinsed with 100 mL in 1N NaHSO3 and dried to give the title compound as a yellow solid.

Workup

  1. temperaturethe resulting mixture refluxed at 100°-130 C.°C
  2. waitfor 40 hours
  3. stirringstirred
  4. filtrationThe product was collected by suction filtration
  5. washrinsed with 100 mL in 1N NaHSO3
  6. customdried

Sources & evidence

ORD record
ord-3b66cc6a60ef461eb7ac648a6657c7f6
Source dataset
uspto-grants-1997_09
Patent number
US05663347

Reaction notes

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