Hydrochloric Acid → 1-Hydroxy-4-methoxypyrid-2-one

HRID 483759Notes

Reaction equation

HRID 483759 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N+:3]=1[O-:10].[OH-:11].[Na+].Cl>>[OH:10][N:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]1=[O:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15593755Pyridine, 2-chloro-4-methoxy-, 1-oxide

Product 1

HCID 155937561-Hydroxy-4-methoxypyrid-2-oneYield 20%

Procedure

2-Chloro-4-methoxypyridine-1-oxide (3.3 g) is dissolved in 10% w/v aqueous NaOH (33 ml) and the mixture is heated on a steam bath for 3.5 hours when it is cooled and acidified with concentrated HCl to a pH of 2.5 to yield white crystals. Recrystallisation of these from water gives 1-hydroxy-4-methoxypyrid-2-one (0.75 g, 20%), m.p. 174°-175° C., δ(D2O) 5.9 (s, 1H), 6.00 (q, 1H), 7.5 (d, 1H).

Workup

  1. temperaturethe mixture is heated on a steam bath for 3.5 hours when it
  2. temperatureis cooled
  3. customto yield white crystals
  4. customRecrystallisation of these from water

Sources & evidence

ORD record
ord-9b3db28df25c4297a8796f79456c3a67
Source dataset
uspto-grants-1993_07
Patent number
USRE034313

Reaction notes

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