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

HRID 2106814Notes

Reaction equation

HRID 2106814 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-3-pyridinecarboxylic 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-372132b3f8f54acaa5a0d40763d01387
Source dataset
uspto-grants-1990_06
Patent number
US04931453

Reaction notes

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