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

HRID 1590025Notes

Reaction equation

HRID 1590025 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-92a760632a6a43308a732c6c2a217a8d
Source dataset
uspto-grants-1993_04
Patent number
US05202243

Reaction notes

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