Hydrochloric Acid → HCID 15593757, compound

HRID 279836Notes

Reaction equation

HRID 279836 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][O:11][CH3:12])[CH:5]=[CH:4][N+:3]=1[O-:13].[OH-:14].[Na+].Cl>>[OH:13][N:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH2:10][O:11][CH3:12])=[CH:7][C:2]1=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19751106HCID 19751106, compound

Product 1

HCID 15593757HCID 15593757, compoundYield 29%

Procedure

2-Chloro-4-(2'-methoxyethoxy)-pyridine-1-oxide is treated with 10% w/v aqueous NaOH and the mixture is heated on a steam bath for 3 hours. The resulting solution is acidified to pH 2 with concentrated HCl, then reduced in volume by evaporating in vacuo and left to crystallise. The resultant white solid is recrystallised from ethanol to give 1-hydroxy-4-(2'-methoxyethoxy)-pyrid-2-one (0.58 g, 29%), m.p. 134° C., δ(CDCl3) 3.42 (s, 3H), 3.7 (t, 1H), 4.08 (t, 1H), 6.05 (d, 1H), 6.05 (q, 1H), 7.62 (t, 1H).

Workup

  1. temperaturethe mixture is heated on a steam bath for 3 hours
  2. customby evaporating in vacuo
  3. waitleft
  4. customto crystallise
  5. customThe resultant white solid is recrystallised from ethanol

Sources & evidence

ORD record
ord-0c16fd256eda41d6aef501b1fca2c7a4
Source dataset
uspto-grants-1986_05
Patent number
US04587240

Reaction notes

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