Sodium Methoxide → HCID 67026601, compound

HRID 2113418Notes

Reaction equation

HRID 2113418 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[N+:4]([O-:10])[C:3]=1[C:11]([O:13][CH3:14])=[O:12].[CH3:15][O-:16].[Na+]>CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:16][CH3:15])=[N+:4]([O-:10])[C:3]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 67026662HCID 67026662, compound

Product 1

HCID 67026601HCID 67026601, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 3-chloro-6-(chloromethyl)pyridine-2-carboxylate 1-oxide (1.50 g, 6.35 mmol) in methanol (15 mL) was cooled to 0° C. A 25% solution of sodium methoxide in methanol (1.52 mL) was added and the mixture stirred at room temperature for 6 days. The reaction mixture was diluted with ethyl acetate and washed with water. To the aqueous layer was added brine solution and was extracted with ethyl acetate. The organic layers were combined, dried (MgSO4), filtered and concentrated to dryness to give crude methyl 3-chloro-6-(methoxymethyl)pyridine-2-carboxylate 1-oxide (1.14 g, 4.92 mmol) as a yellow oil; 1H NMR (CDCl3): δ 7.50 (d, 1H), 7.40 (d, 1H), 4.60 (s, 2H), 4.10 (s, 3H), 3.50 (s, 3H).

Workup

  1. washwashed with water
  2. additionTo the aqueous layer was added brine solution
  3. extractionwas extracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-877f60a69dc54814a18c0e588286a589
Source dataset
uspto-grants-2008_10
Patent number
US07432227B2

Reaction notes

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