Sodium Methoxide → Methyl-4-methoxy-5-methoxycarbonyl-nicotinate

HRID 6894Notes

Reaction equation

HRID 6894 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:9](Cl)=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:7]=[N:6][CH:5]=1.[CH3:16][O-:17].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:9]([O:17][CH3:16])=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 22019198Dimethyl 4-chloropyridine-3,5-dicarboxylate

Product 1

HCID 22019197Methyl-4-methoxy-5-methoxycarbonyl-nicotinate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.3 g (27.5 mmol) of methyl-4-chloro-5-methoxycarbonyl-nicotinate in 100 ml of THF is added 6.48 ml (35 mmol) of a 5.4 m solution of sodium methoxide in methanol. The mixture is stirred for 10 minutes and evaporated. 100 ml of a 0.25M aqueous HCl is added to the residue. The solution is made basic with K2CO3 and extracted with ethyl acetate. The organic phase is dried and evaporated to give an oil which crystallised on cooling. There is obtained 6,2 g (quantitative yield) of a solid (M+1=226).

Workup

  1. customevaporated
  2. addition100 ml of a 0.25M aqueous HCl is added to the residue
  3. extractionextracted with ethyl acetate
  4. customThe organic phase is dried
  5. customevaporated
  6. customto give an oil which
  7. customcrystallised
  8. temperatureon cooling

Sources & evidence

ORD record
ord-8a45cdf4188e45cba8817e064590da3d
Source dataset
uspto-grants-2006_08
Patent number
US07084163B2

Reaction notes

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