Potassium Iodide → HCID 178524773, compound

HRID 488462

Reaction equation

HRID 488462 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[I:11]([O-])(=O)=O.[K+].[I-].[K+]>O.OS(O)(=O)=O>[OH:1][C:2]1[C:10]([I:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 23665710Potassium IodateHCID 178418479HCID 178418479, compound

Product 1

HCID 178524773HCID 178524773, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
60 °C

Procedure

6-Hydroxynicotinic acid (20 g) in water (200 ml) and H2SO4 (80 ml) was heated to 90° C. for 1 hour. Potassium iodate (0.42 equivalent) and potassium iodide (0.96 equivalent) were both added portionwise over 2 hours. After a further hour at 90° C. the mixture was cooled to 60° C. and added to 1 kg of ice. The brown solid was filtered off, dried and taken up in DMF (30 ml)/EtOH(1 litre). Sodium metabisulfite was added until the brown colour disappeared and the mixture was poured onto ice (2 kg), a further 1.5 litre water added and the white solid filtered to give title compound (16.5 g). NMR δ(DMSO) 12.95 (1H, broad), 12.35 (1H, broad), 8.36 (1H, d), 8.03 (1H, d)

Workup

  1. additionboth added portionwise over 2 hours
  2. filtrationThe brown solid was filtered off
  3. customdried
  4. additionSodium metabisulfite was added until the brown colour
  5. additionthe mixture was poured onto ice (2 kg)
  6. additiona further 1.5 litre water added
  7. filtrationthe white solid filtered

Sources & evidence

ORD record
ord-4d1cf850ac544cdda7fec36221f94862
Source dataset
uspto-grants-2005_12
Patent number
US06972297B2

Linked notes

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