2-Methylpyridin-3-ol → 3-Methoxy-2-methylpyridine

HRID 895824Notes

Reaction equation

HRID 895824 reaction equation
[OH:1][C:2]1[C:3]([CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:9][O-].[Na+]>[Br-].C1([N+](C)(C)C)C=CC=CC=1.CN(C)C=O>[CH3:9][O:1][C:2]1[C:3]([CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 707192-Methylpyridin-3-olHCID 10942334Sodium Methoxide

Product 1

HCID 30152703-Methoxy-2-methylpyridineYield 16.8%

Reagents, catalysts & solvents 2

HCID 27663Benzenaminium, N,N,N-trimethyl-, bromide (1:1)CatalystHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 3-hydroxy-2-methylpyridine (1.0 g, 9.2 mmol), phenyltrimethylammonium bromide (2.2 g, 11 mmol) and sodium methoxide (550 mg, 11 mmol) in dimethylformamide (10 ml) was heated under reflux for 3 hours, then the cool reaction mixture washed with water (40 ml) and extracted with ether (3×40 ml). The combined extracts were dried (Na2SO4) and evaporated under reduced pressure, then the residue purified by column chromatography on silica gel, using hexane:ethyl acetate (1:1) as eluant, to give the title compound (190 mg) as a solid. δ (CDCl3): 2.34 (3H, s), 3.68 (3H, s), 6.93 (2H, m), 7.94 (1H, d). LRMS: m/z 124 (M+1)+.

Workup

  1. temperatureunder reflux for 3 hours
  2. customthe cool reaction mixture
  3. washwashed with water (40 ml)
  4. extractionextracted with ether (3×40 ml)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d9a7b9a3c4e940a0813c827ea1e95d7e
Source dataset
uspto-grants-2005_07
Patent number
US06916927B2

Reaction notes

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