Sodium Iodide → 6-Iodopyridine-3-carboxylic acid

HRID 1698787Notes

Reaction equation

HRID 1698787 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

Conditions

Temperature
115 °C

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. 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. stirringstirred
  2. filtrationThe product was collected by suction filtration
  3. washrinsed with 100 mL in 1N NaHSO3
  4. customdried

Sources & evidence

ORD record
ord-c4976749d7b54137a44d84f5964dc8f8
Source dataset
uspto-grants-2002_02
Patent number
US06344463B1

Reaction notes

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