Acetic Acid → 6-Methyl-1-oxo-1lambda~5~-pyridin-3-ol

HRID 1395187Notes

Reaction equation

HRID 1395187 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.C(O)(=[O:11])C.OO>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N+:3]=1[O-:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 142752-Methyl-5-hydroxypyridine

Product 1

HCID 904066-Methyl-1-oxo-1lambda~5~-pyridin-3-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 100.0 g of 2-methyl-5-hydroxy-pyridine, 600 ml of acetic acid and 200 ml of 30-35% hydrogen peroxide is heated on a steam bath with occasional swirling for 18 hours. Then to the mixture is added 500 ml of water and the resulting solution is evaporated to leave a residue. The last traces of water from the residue are removed azeotropically with isopropanol to give a yellow solid. This solid is recrystallized from ethanol to give 2-methyl-5-hydroxy-pyridine-1-oxide melting at 185°-187°.

Workup

  1. temperatureis heated on a steam bath
  2. customthe resulting solution is evaporated
  3. customto leave a residue
  4. customThe last traces of water from the residue are removed azeotropically with isopropanol
  5. customto give a yellow solid
  6. customThis solid is recrystallized from ethanol

Sources & evidence

ORD record
ord-2cd9cc3fe15842a8a7a9086a40c69c80
Source dataset
uspto-grants-1980_05
Patent number
US04202901

Reaction notes

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