Clopyralid → 3-Chloro-6-methoxypyridine-2-carboxylic acid

HRID 2109933Notes

Reaction equation

HRID 2109933 reaction equation
[Cl:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[CH3:12][O-:13].[Na+]>O1CCOCC1.CO.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([O:13][CH3:12])=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 15553ClopyralidHCID 10942334Sodium Methoxide

Product 1

HCID 513419883-Chloro-6-methoxypyridine-2-carboxylic acid

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 3,6-dichloropyridine-2-carboxylic acid (7.10 mmol 1.36 g) in dioxane (15 mL) was added sodium methoxide (21.31 mmol 1.15 g) in methanol dropwise. The mixture was stirred at 85° C. for 14 h, cooled to rt, and diluted with ethyl acetate and aqueous HCl. The organic layer was washed with water and brine, and dried (MgSO4). Removal of the solvent provided 3-chloro-6-methoxypyridine-2-carboxylic acid which was used in the next step without further purification.

Workup

  1. temperaturecooled to rt
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-7b9b84ca042a4f0ba39c8f2892569e0b
Source dataset
uspto-grants-2009_04
Patent number
US07517878B2

Reaction notes

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