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

HRID 2300309Notes

Reaction equation

HRID 2300309 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-51817676cf0d4b15a92ea18a24ffe4df
Source dataset
uspto-grants-2002_12
Patent number
US06498169B1

Reaction notes

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