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

HRID 981153Notes

Reaction equation

HRID 981153 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:20]/[C:21](/[CH3:28])=[CH:22]\[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(O)CCC>[CH3:28][C:21]1[NH:20][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:22]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

4

Reactant 2

HCID 948623-NitrochalconeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-

Product 1

HCID 9998850Ethyl 1,4-dihydro-2-methyl-4(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylateYield 20.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3-(3-nitrophenyl)-1-phenyl-2-propen1-one (2 g), ethyl 3-aminocrotonate (1.2 g) and n-butanol (20 ml) was refluxed for 6 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 (150 ml) eluting with a mixture of benzene and ethyl acetate (30:1 V/V). The fractions containing the object compound were combined and concentrated under reduced pressure to give ethyl 1,4-dihydro-2-methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate (0.6 g).

Workup

  1. temperaturewas refluxed for 6 hours
  2. customthe reaction mixture was evaporated in vacuo
  3. washeluting with a mixture of benzene and ethyl acetate (30:1 V/V)
  4. additionThe fractions containing the object compound
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea2007d825d44237bada45e8bad76d1a
Source dataset
uspto-grants-1991_02
Patent number
US04990507

Reaction notes

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