Water → 2-Methoxy-6-methylpyridin-3-ol

HRID 416555

Reaction equation

HRID 416555 reaction equation
Cl[C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][O-:11].[Na+].CO.O>C(O)(=O)C>[CH3:10][O:11][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 30157972-Chloro-6-methylpyridin-3-olHCID 23694274Sodium methanolate methanol

Product 1

HCID 234638212-Methoxy-6-methylpyridin-3-olYield 48.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In metal sealed tube were added 2-chloro-3-hyroxy-6-methylpyridine (1-014-02) (22.91 g) and 28% sodium methoxide/methanol solution (120 mL) and the reaction mixture was reacted at 150° C. for 3 days. To the reaction mixture was added ice and water (100 mL) and the reaction mixture was neutralized with acetic acid, and evaporated completely. The residue was purified by silica gel column chromatography (chloroform) to give the desired 2-methoxy-3-hyroxy-6-methylpyridine (1-014-03) (10.44 g, 48.1%). Furthermore, the fraction contained the starting material was reacted in sealed tube again.

Workup

  1. customIn metal sealed tube
  2. customthe reaction mixture was reacted at 150° C. for 3 days
  3. customevaporated completely
  4. customThe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-ef4cb71f106b46b9ad72c703118fd199
Source dataset
uspto-grants-2012_01
Patent number
US08088924B2

Linked notes

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