1-Phenyl-2-buten-1-one → Methyl 4-methyl-2-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate

HRID 981155

Reaction equation

HRID 981155 reaction equation
[NH2:1][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1)=[CH:3][C:4]([O:6][CH3:7])=[O:5].[C:17]1([C:23](=O)[CH:24]=[CH:25][CH3:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)CCC>[CH3:26][C:25]1[CH:24]=[C:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:1]=[C:2]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 710901-Phenyl-2-buten-1-oneHCID 69855994Methyl 3-amino-3-(3-nitrophenyl)prop-2-enoate

Product 1

HCID 10066322Methyl 4-methyl-2-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylateYield 5.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of methyl 3-amino-3-(3-nitrophenyl)acrylate (45 g) and 1-phenyl-2-buten-1-one (44 g) in n-butanol (450 ml) was refluxed for 4 hours. After allowing to cool at ambient temperature, the reaction mixture was evaporated in vacuo. The residue was subjected to a column chromatography on silica gel (500 g) eluting with benzene. The fractions containing the object compound were combined and concentrated under reduced pressure to give methyl 4-methyl-2-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate (4.10 g).

Workup

  1. temperaturewas refluxed for 4 hours
  2. customthe reaction mixture was evaporated in vacuo
  3. washeluting with benzene
  4. additionThe fractions containing the object compound
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-61e2f58126c743d3a59936b1db4d8317
Source dataset
uspto-grants-1991_02
Patent number
US04990507

Linked notes

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