Methyl iodide → Methyl 2-chloropyridine-4-carboxylate

HRID 602377Notes

Reaction equation

HRID 602377 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[C:11](=O)([O-])[O-].[K+].[K+].CI.C(OCC)(=O)C>CN(C=O)C.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([O:7][CH3:11])=[O:6]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2369852-Chloroisonicotinic acid

Product 1

HCID 2736842Methyl 2-chloropyridine-4-carboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-Chloroisonicotinic acid (300 mg, 1.91 mmol), potassium carbonate (790 mg, 5.72 mmol) and methyl iodide (360 μL, 5.72 mmol) was dissolved in DMF (4.5 mL) and the solution was stirred at room temperature for 4 hours. The reaction mixture was added with saturated brine and ethyl acetate, and the organic layer was separated, followed by washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to obtain methyl 2-chloroisonicotinate (320 mg, 98%).

Workup

  1. customthe organic layer was separated
  2. washby washing with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-084e601d8ada40249ee1d23c06e60759
Source dataset
uspto-grants-2011_03
Patent number
US07906522B2

Reaction notes

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