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

HRID 1753904Notes

Reaction equation

HRID 1753904 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(=O)([O-])[O-].[K+].[K+].[CH2:19](I)[CH3:20].O>CN(C)C=O>[CH2:19]([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])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 6761212,6-Dichloro-4-methylpyridine-3-carboxylic acid

Product 1

HCID 70700301Ethyl 2,6-dichloro-4-methylnicotinateYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,6-dichlor-4-methylpyridin-3-carboxylic acid (100 g, 485 mmol) and potassium carbonate (100 g, 728 mmol) in dimethylformamide (1.25 I) is stirred for 30 h at RT before ethyl iodide (59.5 ml, 728 mmol) is added and stirring is continued for 18 h. After completion of the reaction, water is added and the mixture is extracted with ethyl acetate (3×). The combined organic layers are washed with water (2×) and brine (1×), dried over magnesium sulphate and evaporated to dryness to yield 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid ethyl ester (112 g), which was used without further purification.

Workup

  1. additionis added
  2. additionis added
  3. extractionthe mixture is extracted with ethyl acetate (3×)
  4. washThe combined organic layers are washed with water (2×) and brine (1×)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-28981a85e8064fbab441185c086ed825
Source dataset
uspto-grants-2015_10
Patent number
US09168259B2

Reaction notes

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