Dimethyl Sulfate → Methyl 2,6-dichloropyridine-3-carboxylate

HRID 2390899Notes

Reaction equation

HRID 2390899 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>CC(C)=O>[CH3:12][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([Cl:11])=[N:10][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 11106516Methyl 2,6-dichloropyridine-3-carboxylateYield 88.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the mixture of 2,6-dichloro-nicotinic acid (4.7 g, 22 mmol) and acetone (22 ml), potassium carbonate (4.6 g, 33 mmol) and dimethylsulfate (2.4 ml, 24 mmol) were sequentially added at room temperature, and the obtained reaction mixture was stirred at room temperature for 16 hours. Impurities were removed by filtration, and the solvents were evaporated under reduced pressure from the filtrate. Dichloromethane was added to the obtained residue, followed by washing with a saturated sodium bicarbonate aqueous solution. The obtained organic layer was dried using anhydrous sodium sulfate, and the solvents were evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography (heptane:ethyl acetate=10:1 to 1:1), thereby obtaining the entitled compound (4.0 g, 87%).

Workup

  1. additionwere sequentially added at room temperature
  2. customthe obtained reaction mixture
  3. customImpurities were removed by filtration
  4. customthe solvents were evaporated under reduced pressure from the filtrate
  5. additionDichloromethane was added to the obtained residue
  6. washby washing with a saturated sodium bicarbonate aqueous solution
  7. customThe obtained organic layer was dried
  8. customthe solvents were evaporated under reduced pressure
  9. customThe obtained residue was purified with silica gel column chromatography (heptane:ethyl acetate=10:1 to 1:1)

Sources & evidence

ORD record
ord-1db7821aefea4ac28c393c2b47c28f9c
Source dataset
uspto-grants-2012_09
Patent number
US08273885B2

Reaction notes

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