Water → Methyl 2,6-dichloro-4-methylnicotinate

HRID 1753894Notes

Reaction equation

HRID 1753894 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[C:4]([Cl:12])[N:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[CH3:13][O:9][C:8]([C:7]1[C:2]([Cl:1])=[N:3][C:4]([Cl:12])=[CH:5][C:6]=1[CH3:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6761212,6-Dichloro-4-methylpyridine-3-carboxylic acid

Product 1

HCID 46911843Methyl 2,6-dichloro-4-methylnicotinateYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.0 g (24.3 mmol) 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid in DMF (73 ml) were added 5.0 g (36.4 mmol) K2CO3 and 7.6 ml (121.3 mmol) iodomethane at 0° C. The reaction mixture was stirred at RT for 3 h and was subsequently poured into water. This mixture was extracted with EtOAc and the organic layer was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 19:1) provided 5.2 g (23.7 mmol, 98%) 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid methylester.

Workup

  1. extractionThis mixture was extracted with EtOAc
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by CC (hexane/EtOAc 19:1)

Sources & evidence

ORD record
ord-7c438414ed124666b0112b7f8e854371
Source dataset
uspto-grants-2015_10
Patent number
US09168259B2

Reaction notes

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