Methanol → Methyl 2-methoxy-5-ethyl-6-methylnicotinate

HRID 2379675Notes

Reaction equation

HRID 2379675 reaction equation
[Na].Cl[C:3]1[N:12]=[C:11]([CH3:13])[C:10]([CH2:14][CH3:15])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[CH3:16][OH:17]>>[CH3:16][O:17][C:3]1[N:12]=[C:11]([CH3:13])[C:10]([CH2:14][CH3:15])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 5360545SodiumHCID 15228412Methyl 2-chloro-5-ethyl-6-methylpyridine-3-carboxylate

Product 1

HCID 15228413Methyl 2-methoxy-5-ethyl-6-methylnicotinateYield 73%

Procedure

To a solution of sodium metal (0.55 g, 24 mmol) dissolved in anhydrous methanol (15 mL), under a nitrogen atmosphere, was added a solution of methyl 2-chloro-5-ethyl-6-methylnicotinate (3.18 g, 14.9 mmol) in dry methanol (5 mL). This solution was refluxed and monitored by tlc (thin layer chromatogram) until the starting material had been consumed (about 24 hours). The cooled mixture was diluted with diethyl ether (50 mL), washed with water, saturated aqueous NaHCO3, dried (Na2SO4), filtered and the solvent evaporated to yield 2.28 g (73%) of pure product as a light yellow oil.

Workup

  1. temperatureThis solution was refluxed
  2. customhad been consumed (about 24 hours)
  3. additionThe cooled mixture was diluted with diethyl ether (50 mL)
  4. washwashed with water, saturated aqueous NaHCO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-055c0c01b8584507b83b0dee31c6425d
Source dataset
uspto-grants-1994_11
Patent number
US05364776

Reaction notes

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