Ethyl cyanoacetate → HCID 13233233, compound

HRID 1731551Notes

Reaction equation

HRID 1731551 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[CH:7]=[C:8]([C:22]([CH3:24])=[O:23])[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:10])([O-:3])=[O:2].[C:28]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])#[N:29].N1CCCCC1>C(O)C>[NH2:29][C:28]1[O:23][C:22]([CH3:24])=[C:8]([C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:10])[CH:7]([C:6]2[CH:25]=[CH:26][CH:27]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:30]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 54012662HCID 54012662, compound

Product 1

HCID 13233233HCID 13233233, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5.7 g (15 mmol) of decyl 2-(3-nitrobenzylidene)acetoacetate and 1.8 g (15 mmol) of ethyl cyanoacetate in 15 ml of ethanol was heated to boiling in the presence of 0.3 ml of piperidine, for 4 hours. The solvent was then removed by distillation and the oily residue was purified by column chromatography (SiO2, chloroform) and brought to crystalli ation, melting point: 100° C., yield: 3.3 g (45%).

Workup

  1. customThe solvent was then removed by distillation
  2. customthe oily residue was purified by column chromatography (SiO2, chloroform)

Sources & evidence

ORD record
ord-5b85ce6a22ca4d0fb3d2be3a4de5f5ba
Source dataset
uspto-grants-1986_11
Patent number
US04622332

Reaction notes

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