Water → Methyl 2-methoxyisonicotinate

HRID 1635490Notes

Reaction equation

HRID 1635490 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:12][O-:13].[Na+].O>O1CCOCC1>[CH3:12][O:13][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 2736842Methyl 2-chloropyridine-4-carboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 14223465Methyl 2-methoxyisonicotinateYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 2-chloroisonicotinate (5.23 g, 0.030 mol) and sodium methoxide (2.47 g, 0.045 mol) in 15 mL of dioxane was heated at reflux for 1.5 hours. After the reaction mixture was cooled, water was added and the resulting mixture was extracted with methylene chloride. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give 3.76 g (75%) of product as a yellow oil: Anal. Calc'd. for C8H9NO3: C, 57.48; H, 5.43; N, 8.38. Found: C, 57.07; H, 5.54; N, 8.34.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureAfter the reaction mixture was cooled
  4. extractionthe resulting mixture was extracted with methylene chloride
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-05a75eb72c374d90b063afae6d5f8dbf
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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