Iodine → 2-Iodo-6-methylpyridin-3-ol

HRID 1913430Notes

Reaction equation

HRID 1913430 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[I:15]I>O>[I:15][C:6]1[C:5]([OH:8])=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 10340Sodium CarbonateHCID 142752-Methyl-5-hydroxypyridine

Product 1

HCID 899572-Iodo-6-methylpyridin-3-olYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 6-methylpyridin-3-ol (235 g, 2.75 mol) and water (5.28 L) at 0° C. was added Na2CO3 (440 g, 5.5 mol) and the mixture was stirred at room temperature for 30 minutes. A solution of I2 (760 g, 3.85 mol) and KI (760 g, 5.83 mol) in water (5.28 L) was added dropwise to the reaction over a period of 1 hour. The mixture was stirred at room temperature for 3 hours and the resulting precipitate was collected by filtration to afford 2-iodo-6-methylpyridin-3-ol (390 g, 77.0%) as a yellow solid which was used without further purification.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-ca3452c04d02459495882be8046f5688
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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