Ethyl 2-(3-nitrobenzylidene)-3-oxobutanoate → Decyl ethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

HRID 1731549Notes

Reaction equation

HRID 1731549 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[CH:7]=[C:8]([C:14]([CH3:16])=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])([O-:3])=[O:2].[NH2:20]/[C:21](/[CH3:36])=[CH:22]\[C:23]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:24]>C(O)C>[CH3:36][C:21]1[NH:20][C:14]([CH3:16])=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]([C:6]2[CH:17]=[CH:18][CH:19]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:22]=1[C:23]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:24]

Participants

4

Reactant 2

HCID 367507Ethyl 2-(3-nitrobenzylidene)-3-oxobutanoateHCID 86741101Decyl 3-aminocrotonate

Product 1

HCID 13233215Decyl ethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 263 g (1 mol) of ethyl 2-(3-nitrobenzylidene)acetoacetate and 241 g (1 mol) of decyl 3-aminocrotonate in 2.4 liters of absolute ethanol was heated to boiling under nitrogen for 18 hours. The mixture was then filtered hot and the filtrate was evaporated in vacuo to about one half of the volume. The concentrated solution was cooled in ice, producing a thick mass of crystals. This was filtered off with suction, recrystallized from ethanol and, after washing with 0.5 liters of n-hexane, was dried in a vacuum oven at 60° C.

Workup

  1. filtrationThe mixture was then filtered hot
  2. customthe filtrate was evaporated in vacuo to about one half of the volume
  3. temperatureThe concentrated solution was cooled in ice
  4. customproducing a thick mass of crystals
  5. filtrationThis was filtered off with suction
  6. customrecrystallized from ethanol
  7. washafter washing with 0.5 liters of n-hexane
  8. customwas dried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-8e4b9292e3384b1f80ec65014ab370ea
Source dataset
uspto-grants-1986_11
Patent number
US04622332

Reaction notes

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