Potassium Hydroxide → 2-Methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylic acid

HRID 1722775Notes

Reaction equation

HRID 1722775 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[CH:5]=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:3]=1.[OH-].[K+]>C(O)C>[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[CH:5]=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 10248079Ethyl 2-methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate

Product 1

HCID 104720472-Methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylic acidYield 46.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate (4.6 g), aqueous potassium hydroxide (1.07 g in 200 ml water) and ethanol (92 ml) was refluxed for 6 hours. After allowing to cool to ambient temperature, the reaction mixture was washed with ethyl acetate (150 ml×2). The separated aqueous layer was adjusted to pH 3.0 with 10% hydrochloric acid. To this mixture was added acetic acid (40 ml) and stirred for 30 minutes under ice cooling. The resulting precipitates were collected by filtration, washed with water and dried in vacuo to give 2-methyl-4-(3-nitrophenyl)-6-phenyl-3pyridinecarboxylic acid (1.98 g).

Workup

  1. temperaturewas refluxed for 6 hours
  2. washthe reaction mixture was washed with ethyl acetate (150 ml×2)
  3. additionTo this mixture was added acetic acid (40 ml)
  4. customThe resulting precipitates
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-1265deff657a4dc588613b47f926d152
Source dataset
uspto-grants-1989_08
Patent number
US04857527

Reaction notes

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