Sodium ethoxide → Methyl 6-chloro-4-methoxypyridine-3-carboxylate

HRID 1691672Notes

Reaction equation

HRID 1691672 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=[C:4]([Cl:12])[CH:3]=1.[O-:13][CH2:14]C.[Na+]>C1COCC1>[Cl:12][C:4]1[CH:3]=[C:2]([O:13][CH3:14])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 2764083Methyl4,6-dichloronicotinate

Product 1

HCID 22498691Methyl 6-chloro-4-methoxypyridine-3-carboxylateYield 34.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 500 mg of methyl 4,6-dichloronicotinate and 5.0 mL of THF was added dropwise 157 mg of sodium ethoxide (28 wt % of methanol solution) under cooling in an ice bath. It was warmed to room temperature, followed by stirring overnight. The reaction mixture was concentrated under reduced pressure, and the residue was then purified by silica gel column chromatography to obtain 162 mg of methyl 6-chloro-4-methoxynicotinate as a white solid.

Workup

  1. temperatureunder cooling in an ice bath
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9f17b857bd4c4b43861922cbb7da4b7e
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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