Iodine → 6-Chloro-2-iodo-3-hydroxypyridine

HRID 611568Notes

Reaction equation

HRID 611568 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[I:15]I>O>[Cl:1][C:2]1[N:3]=[C:4]([I:15])[C:5]([OH:8])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 807Iodine2×HCID 10340Sodium CarbonateHCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 234331586-Chloro-2-iodo-3-hydroxypyridineYield 54.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-chloro-5-hydroxypyridine (5 g, from step 11b) and 8.6 g of Na2CO3 in 100 mL of water was added 9.8 g of I2. The mixture was stirred until the iodine color disappeared. The reaction mixture was then adjusted to pH 5 and extracted with EtOAc. The extract was dried over MgSO4, and the solvent was removed. The residue was recrystallized from MeOH to afford 5.4 g of the title compound: 1H NMR (CD3OD, 300 MHz) δ 7.09 (d, 1H, J=8.5 Hz), 7.20 (d, 1H, J=8.5 Hz); 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 MeOH

Sources & evidence

ORD record
ord-93a08cd083bd431994e1dd4685b977fd
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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