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

HRID 1937677Notes

Reaction equation

HRID 1937677 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-79a0d45d7036411ca8e617399884d9e8
Source dataset
uspto-grants-2002_05
Patent number
US06395753B1

Reaction notes

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