Water → 2-Methoxy-4,6-dimethylnicotinic acid

HRID 372212Notes

Reaction equation

HRID 372212 reaction equation
[CH3:1][O:2][C:3]1[N:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:4]=1[C:5]#N.[OH-:13].[K+].[OH2:15]>C(O)C>[CH3:1][O:2][C:3]1[N:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:4]=1[C:5]([OH:15])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 5952762-Methoxy-4,6-dimethylnicotinonitrile

Product 1

HCID 27285162-Methoxy-4,6-dimethylnicotinic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

97 g (0.6 mole) of 2-methoxy-4,6-dimethylnicotinonitrile and 230 g of solid potassium hydroxide are dissolved in 1000 ml of ethanol and 120 ml of water and the solution is refluxed under nitrogen for 82 hours. The mixture is cooled, the precipitated substance collected by filtration, and the bulk of the ethanol is distilled off from the filtrate in vacuo. The residue is dissolved in 500 ml of water and extracted with methylene chloride. The alkaline aqueous phase is adjusted to pH 3.3 with concentrated hydrochloric acid and the precipitated crude product is collected by filtration. Recrystallisation of this crude product from ethanol yields pure 2-methoxy-4,6-dimethylnicotinic acid (m.p. 210°-215° C).

Workup

  1. temperatureThe mixture is cooled
  2. filtrationthe precipitated substance collected by filtration
  3. distillationthe bulk of the ethanol is distilled off from the filtrate in vacuo
  4. dissolutionThe residue is dissolved in 500 ml of water
  5. extractionextracted with methylene chloride
  6. customthe precipitated crude product
  7. filtrationis collected by filtration
  8. customRecrystallisation of this crude product from ethanol

Sources & evidence

ORD record
ord-91c318a28e194d14b05b3d54c56bb2a5
Source dataset
uspto-grants-1978_05
Patent number
US04089960

Reaction notes

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