Acetic Acid → Ethyl 3-(4-aminophenyl)-2-cyanoacrylate

HRID 133685

Reaction equation

HRID 133685 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11].C(NCC)C.C(O)(=O)C>C(O)C>[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:12]([C:10]#[N:11])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 8021DiethylamineHCID 111584-Aminobenzaldehyde

Product 1

HCID 3540149Ethyl 3-(4-aminophenyl)-2-cyanoacrylateYield 83.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

36 g (0.3 mol) of para-aminobenzaldehyde are suspended in 300 ml of ethanol. 33.9 g (0.3 mol) of ethyl cyanoacetate and a mixture of 0.375 ml of diethylamine and 1.125 ml of acetic acid, as catalyst, are added to the suspension. The reaction mixture is refluxed for 2 hours, left to cool and then crystallized. After separating out the crystals by filtration and drying, 53.9 g (83% yield) of ethyl 3-(4-aminophenyl)-2-cyanoacrylate are obtained in the form of orange-coloured crystals.

Workup

  1. additionas catalyst, are added to the suspension
  2. temperatureThe reaction mixture is refluxed for 2 hours
  3. waitleft
  4. temperatureto cool
  5. customcrystallized
  6. customAfter separating out the crystals by filtration
  7. customdrying

Sources & evidence

ORD record
ord-6fe060502bb841b5a49f1768c8a4f508
Source dataset
uspto-grants-2008_06
Patent number
US07390916B2

Linked notes

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