Ethyl cyanoacetate → Ethyl 4-acetamido-alpha-cyanocinnamate

HRID 352997Notes

Reaction equation

HRID 352997 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[C:9]([NH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1)(=[O:11])[CH3:10].N1CCCCC1>C(O)C>[C:9]([NH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[C:3]([C:1]#[N:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:15][CH:14]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 739424-Acetamidobenzaldehyde

Product 1

HCID 245851Ethyl 4-acetamido-alpha-cyanocinnamateYield 41.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 33.9 g (0.3 mol) of ethyl cyanoacetate and 59.1 g (0.3 mol) of 4-acetamidobenzaldehyde in 300 ml of ethanol in the presence of 5 ml of piperidine is refluxed for 3 hours. The very viscous medium is diluted with 800 ml of hot ethanol. It is filtered while hot. The yellow solid obtained is washed with hot ethanol. After filtration and drying, 32 g (41% yield) of ethyl 3-(4-acetylaminophenyl)-2-cyanoacrylate are obtained in the form of a pale yellow powder.

Workup

  1. temperatureis refluxed for 3 hours
  2. filtrationIt is filtered while hot
  3. customThe yellow solid obtained
  4. washis washed with hot ethanol
  5. filtrationAfter filtration
  6. customdrying

Sources & evidence

ORD record
ord-c3920152b35949dc83c01c3200927c64
Source dataset
uspto-grants-2004_06
Patent number
US06749839B2

Reaction notes

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