Ethyl 1,4-dihydro-2-methyl-4(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate → Ethyl 2-methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate

HRID 981156Notes

Reaction equation

HRID 981156 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:5][CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[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 1

HCID 9998850Ethyl 1,4-dihydro-2-methyl-4(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate

Product 1

HCID 10248079Ethyl 2-methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylateYield 50.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of ethyl 1,4-dihydro-2-methyl-4(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate (0.5 g) in chloroform (5 ml) was added activated manganese dioxide (2 g) and the mixture was refluxed for 1 hour with stirring vigorously. After allowing to cool to ambient temperature, manganese dioxide was filtered off and the filtrate was evaporated in vacuo. The residual precipitates were recrystallized from ethanol, washed with ethanol and dried in vacuo to give ethyl 2-methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate (0.25 g)

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. filtrationmanganese dioxide was filtered off
  3. customthe filtrate was evaporated in vacuo
  4. customThe residual precipitates
  5. customwere recrystallized from ethanol
  6. washwashed with ethanol
  7. customdried in vacuo

Sources & evidence

ORD record
ord-5354746d50cb4d14883209288639118d
Source dataset
uspto-grants-1991_02
Patent number
US04990507

Reaction notes

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