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

HRID 1692387Notes

Reaction equation

HRID 1692387 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].[C:13](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH3:13][O:5][C:4](=[O:6])[C:3]1[C:7]([CH3:12])=[CH:8][C:9]([Cl:11])=[N:10][C:2]=1[Cl:1]

Participants

5

Reactant 3

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

Product 1

HCID 46911843Methyl 2,6-dichloro-4-methylnicotinateYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8.05 g (39.1 mmol) of 2,6-dichloro-4-methyl-nicotinic acid [Lamm, G. Ger. Offen. (1977), DE 2538950] in 100 ml of DMF was added 8.10 g (58.6 mmol) of potassium carbonate. While stirring, 12.16 ml=27.7 g (195.4 mmol) of iodomethane was added drop by drop and the reaction mixture was stirred for 6 hours at RT. It was then poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated to give 8.47 g (99%) of the title compound as light yellow solid. MS: 219.0 (M+, 2Cl).

Workup

  1. stirringthe reaction mixture was stirred for 6 hours at RT
  2. additionIt was then poured
  3. extractionextracted twice with EtOAc
  4. washthe organic phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-752b668f7e774f549b5d8367a486a554
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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