Sodium Hydroxide → 2-(4-Chloro-3,5-dimethoxyphenyl)isonicotinic acid

HRID 984164Notes

Reaction equation

HRID 984164 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][N:20]=2)[C:13]([O:15]CC)=[O:14])=[CH:4][C:3]=1[O:21][CH3:22].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[C:3]([O:21][CH3:22])=[CH:4][C:5]([C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][N:20]=2)[C:13]([OH:15])=[O:14])=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22557799Ethyl 2-(4-chloro-3,5-dimethoxyphenyl)isonicotinate

Product 1

HCID 225580392-(4-Chloro-3,5-dimethoxyphenyl)isonicotinic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(4-chloro-3,5-dimethoxyphenyl)isonicotinate (8.55 g) in ethanol (80 mL) was added 2 M sodium hydroxide (100 mL). The mixture was refluxed for 30 min and evaporated. The aqueous layer was neutralized by 1 M hydrochloric acid and precipitates were dissolved in a mixed solvent of ethyl acetate-THF (3:1). After drying over anhydrous sodium sulfate, the solvent was evaporated to give the title compound.

Workup

  1. temperatureThe mixture was refluxed for 30 min
  2. customevaporated
  3. customprecipitates
  4. dissolutionwere dissolved in a mixed solvent of ethyl acetate-THF (3:1)
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-040110b68cd14253a4d8b49b4cb57bfc
Source dataset
uspto-grants-2005_03
Patent number
US06867221B2

Reaction notes

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