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

HRID 1762149Notes

Reaction equation

HRID 1762149 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-24f2c8e5ef1d4d1bbbd52d8f3ec1754c
Source dataset
uspto-grants-1989_05
Patent number
US04831030

Reaction notes

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