Sodium Methoxide → Methyl 2,6-dichloro-4-methoxynicotinate

HRID 80829Notes

Reaction equation

HRID 80829 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([Cl:12])[CH:9]=[C:8](Cl)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:14][O-:15].[Na+]>CO>[Cl:1][C:2]1[N:11]=[C:10]([Cl:12])[CH:9]=[C:8]([O:15][CH3:14])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 71304377Methyl 2,4,6-trichloronicotinate

Product 1

HCID 86690279Methyl 2,6-dichloro-4-methoxynicotinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2,4,6-trichloronicotinate [(5.04 g, 20.96 mmol), prepared as described in WO2010/31589] in methanol (52 mL) was added the sodium methoxide (25 wt % in methanol, 5.04 mL, 22.0 mmol) at room temperature. The cloudy white mixture was stirred for 17 h, then partitioned between EtOAc and water. The layers were separated and the aqueous layer was further extracted with EtOAc (2×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified by FCC (0-20% EtOAc:heptane) to provide methyl 2,6-dichloro-4-methoxynicotinate. MS (ESI+) m/z 236.1 (M+H)+.

Workup

  1. custompartitioned between EtOAc and water
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with EtOAc (2×)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by FCC (0-20% EtOAc:heptane)

Sources & evidence

ORD record
ord-66422f9133814f869d803f2cca1e4769
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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