Sodium Methoxide → Methyl 6-chloro-2-methoxynicotinate

HRID 1691664Notes

Reaction equation

HRID 1691664 reaction equation
Cl[C:2]1[N:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7]C)=[O:5].[CH3:14][O-:15].[Na+]>C(Cl)Cl>[Cl:13][C:11]1[CH:10]=[CH:9][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([O:15][CH3:14])[N:12]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 12263987Ethyl 2,6-dichloronicotinate

Product 1

HCID 10560015Methyl 6-chloro-2-methoxynicotinateYield 55.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.00 g of ethyl 2,6-dichloronicotinate was dissolved in 10 mL of methylene chloride, and 1.05 g of sodium methoxide (28 wt % of methanol solution) was added thereto at room temperature. After stirring at room temperature for 2 days, the reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 511 mg of methyl 6-chloro-2-methoxynicotinate as a white solid.

Workup

  1. customat room temperature
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-ef31076e86da4265b1d3d82b4a8b294f
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

Loading…