Sodium Hydroxide → 5-Hydroxy-2-methoxypyridine

HRID 1106607

Reaction equation

HRID 1106607 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 x). 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 x)
  3. washThe combined CHCl3 extracts were washed with H2O, dried(anhydrous MgSO4) and
  4. customevaporated

Sources & evidence

ORD record
ord-a0fc49c836644fa49a69eaac378a3d51
Source dataset
uspto-grants-2000_05
Patent number
US06057319

Linked notes

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