Sodium Hydroxide → 4-Chloro-3,5-dimethylpicolinic Acid

HRID 2304816Notes

Reaction equation

HRID 2304816 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([C:9]([O:11]CC)=[O:10])[C:3]=1[CH3:14].[OH-].[Na+]>>[C:9]([C:4]1[C:3]([CH3:14])=[C:2]([Cl:1])[C:7]([CH3:8])=[CH:6][N:5]=1)([OH:11])=[O:10]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 10220000Ethyl 4-chloro-3,5-dimethylpicolinate

Product 1

HCID 103134284-Chloro-3,5-dimethylpicolinic AcidYield 85%

Procedure

4-Chloro-2-Ethoxycarbonyl-3,5-Lutidine (1 eq.) was suspended in 10% sodium hydroxide aqueous solution (4 eq.), the mixture was stirred and heated to 80ℑ C. After 4 hours a homogeneoussolution was obtained. The solution was washed with toluene and then acidified to pH 2.5. The white precipitate was extracted with dichloromethane (3×5 volumes). The combined organic extracts were dried over sodium sulfate, filtered and the solvent was evaporated under vacuum. The 2-carboxy-4-chloro-3,5-lutidine product was obtained as an off white solid in 85% yield.

Workup

  1. temperatureheated to 80ℑ C
  2. customAfter 4 hours a homogeneoussolution was obtained
  3. washThe solution was washed with toluene
  4. extractionThe white precipitate was extracted with dichloromethane (3×5 volumes)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-2f48404459b54c90aea9ab0113cc0517
Source dataset
uspto-grants-2002_08
Patent number
US06437139B1

Reaction notes

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