Hydrochloric Acid → 4-Methyl-2-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylic acid

HRID 2106815Notes

Reaction equation

HRID 2106815 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]([O:25]C)=[O:24].[OH-].[Na+].O1CCOCC1.Cl>C(O)(=O)C.C(Cl)(Cl)Cl.O.CO>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]([OH:25])=[O:24]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 10066322Methyl 4-methyl-2-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate

Product 1

HCID 103595154-Methyl-2-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylic acidYield 71.5%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of methyl 4-methyl-2-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate (4.08 g), aqueous sodium hydroxide (0.94 g in 10 ml water), dioxane (20 ml) and methanol (80 ml) was refluxed for 14 hours. After allowing to cool to ambient temperature, the reaction mixture was poured into a mixture of water (150 ml) and chloroform (100 ml). The separated aqueous layer was adjusted to pH 2.9 with 10% aqueous hydrochloric acid. To this mixture was added acetic acid (15 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 4-methyl-2-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylic acid (2.80 g).

Workup

  1. temperaturewas refluxed for 14 hours
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-10e1e2421b9144e58b51bf885a75f2de
Source dataset
uspto-grants-1990_06
Patent number
US04931453

Reaction notes

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