Iodine → HCID 178517758, compound

HRID 611572Notes

Reaction equation

HRID 611572 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[I:15]I>O>[Cl:1][C:2]1[CH:3]=[C:4]([I:15])[C:5]([OH:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 807Iodine2×HCID 10340Sodium CarbonateHCID 1785160645-chloropyridin-2-ol

Product 1

HCID 178517758HCID 178517758, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 6.48 g sample of 5-chloro-2-pyridinol (Aldrich) and 10.8 g of Na2CO3 were dissolved in 250 mL of water. To this solution was added 12.73 g of I2, and the mixture was stirred until the iodine color disappeared. The reaction mixture was then adjusted to pH 7 and extracted with EtOAc. The extract was dried over MgSO4, and the solvent was removed. The residue was recrystallized from ethanol/water to afford 4 g of the title compound: 1H NMR (DMSO-d6, 300 MHz) δ 7.71 (d,1H), 8.18 (d, 1H); MS m/z: 256 (M+H)+, 273 (M+NH4)+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe extract was dried over MgSO4
  3. customthe solvent was removed
  4. customThe residue was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-6604563e5ace40f88fb9440e2678f04a
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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