Malononitrile → 4-Phenyl-1-(3-ethoxyphenyl)-2-amino-3-cyanopyrrole

HRID 362300Notes

Reaction equation

HRID 362300 reaction equation
[Na].[C:2](#[N:6])[CH2:3][C:4]#[N:5].[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23](=O)[CH3:24])[CH:13]=[CH:14][CH:15]=1)[CH3:8]>C(O)C>[C:21]1([C:22]2[C:3]([C:4]#[N:5])=[C:2]([NH2:6])[N:16]([C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH2:7][CH3:8])[CH:11]=3)[CH:17]=2)[CH:20]=[CH:19][CH:18]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 5360545SodiumHCID 540308002'-(3-Ethoxyphenylamino)acetophenone

Product 1

HCID 545359574-Phenyl-1-(3-ethoxyphenyl)-2-amino-3-cyanopyrrole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

0.4 g of sodium is dissolved in 70 ml of ethanol and subsequently first 1.24 g of malononitrile and then 4.0 g of 2'-(3-ethoxyphenylamino)acetophenone are added at RT and the mixture is stirred at 50° C. for 2 h. The mixture is then cooled and concentrated in an RE. The residue is partitioned between water and methylene chloride and the aqueous phase is extracted twice with methylene chloride. The combined organic phases are dried over Na2SO4 and concentrated, 4-phenyl-1-(3-ethoxyphenyl)-2-amino-3-cyanopyrrole being obtained. The oily product is employed in the next stage without further purification.

Workup

  1. temperatureThe mixture is then cooled
  2. concentrationconcentrated in an RE
  3. customThe residue is partitioned between water and methylene chloride
  4. extractionthe aqueous phase is extracted twice with methylene chloride
  5. dry with materialThe combined organic phases are dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3231146dc02c409eb4b4800d937341af
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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