Methyl iodide → Ethyl 5-chloro-6-methoxypicolinate

HRID 70532

Reaction equation

HRID 70532 reaction equation
[CH3:1]I.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][C:9]=1[OH:10]>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][C:9]=1[O:10][CH3:1]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178468879HCID 178468879, compound

Product 1

HCID 46311511Ethyl 5-chloro-6-methoxypicolinateYield 80%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

Silver carbonate (142.4 g) and methyl iodide (25 mL) were added to a solution of ethyl 5-chloro-6-hydroxypyridine-2-carboxylate (26.0 g) in chloroform (500 mL), and the mixture was stirred at 70° C. for seven hours. The reaction solution was filtered through celite, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) and purified again by silica gel column chromatography (hexane:ethyl acetate=20:1) to give ethyl 5-chloro-6-methoxypyridine-2-carboxylate as a white solid (22.3 g, 80%).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1)
  4. custompurified again by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-b708586464974af298207568eeaf91d3
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Linked notes

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