Methyl iodide → Methyl 2-chloro-6-methylpyridine-3-carboxylate

HRID 62847

Reaction equation

HRID 62847 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CI.[C:14]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:14][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([CH3:11])=[N:10][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1217242-Chloro-6-methylnicotinic acid

Product 1

HCID 13055804Methyl 2-chloro-6-methylpyridine-3-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-6-methyl-nicotinic acid (3.58 g, 20.86 mmol) was dissolved in DMF (34 mL). MeI (5.8 mL, 93.88 mmol) and K2CO3(7.78 g, 56.33 mmol) were added thereto, and the mixture was stirred at room temperature for 2 hours. The reactant was distilled under reduced pressure to remove the solvent and extracted with EtOAc. The organic layer was dried with MgSO4, filtered and concentrated under reduced pressure. The obtained residue was purified by column chromatography (eluent EtOAc/Hex=1/2) to obtain the title compound (3.68 g, 94%).

Workup

  1. distillationThe reactant was distilled under reduced pressure
  2. customto remove the solvent
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by column chromatography (eluent EtOAc/Hex=1/2)

Sources & evidence

ORD record
ord-fbfad6ac0e674b76aae3f5c4101743e1
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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