Sodium Hydroxide → 5-Hydroxy-2-methoxypyridine

HRID 376358

Reaction equation

HRID 376358 reaction equation
C([O:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[N:9][CH:10]=1)(=O)C.[OH-].[Na+]>CO>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 224515665-Acetoxy-2-methoxypyridine

Product 1

HCID 116223355-Hydroxy-2-methoxypyridineYield 53.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the 5-acetoxy-2-methoxypyridine(600 mg, 3.59 mmol) in MeOH(10 mL) was added 1M aq. NaOH (10 mL, 10 mmol). After stirring at r.t. for 30 min, volatile solvent was removed in vacuo, acidified with HOAc and extracted with CHCl3(3×). The combined CHCl3 extracts were washed with H2O, dried(anhydrous MgSO4) and evaporated to give the title compound as a brown oil(240 mg, solidified on standing).

Workup

  1. customvolatile solvent was removed in vacuo
  2. extractionextracted with CHCl3(3×)
  3. washThe combined CHCl3 extracts were washed with H2O, dried(anhydrous MgSO4) and
  4. customevaporated

Sources & evidence

ORD record
ord-f79ec0dd0b9e40458cd8ee59575cc942
Source dataset
uspto-grants-2000_02
Patent number
US06020343

Linked notes

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