Sodium Hydroxide → 5-Hydroxy-2-methoxypyridine

HRID 565116

Reaction equation

HRID 565116 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 5acetoxy-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 combind 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 combind CHCl3 extracts were washed with H2O
  4. dry with materialdried (anhydrous MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-7a0e6f87b72e498c8d540f671597e5da
Source dataset
uspto-grants-2001_01
Patent number
US06169188A

Linked notes

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