Ethyl 3-cyano-3-phenylpyruvate → 2-(p-Chlorophenyl)-5-phenyl-3,4-dioxoadiponitrile

HRID 268474

Reaction equation

HRID 268474 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[H-].[Na+].[C:13]([CH:15]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:16](=[O:22])[C:17](OCC)=[O:18])#[N:14]>C(COC)OC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17](=[O:18])[C:16](=[O:22])[CH:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:13]#[N:14])[C:9]#[N:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 22845Ethyl 3-cyano-3-phenylpyruvateHCID 24758Sodium hydrideHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 215091012-(p-Chlorophenyl)-5-phenyl-3,4-dioxoadiponitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 6.6 g. (0.044 mol.) of p-chlorophenylacetonitrile and 20 ml. of dry glyme was added 6.2 g. (0.13 mol.) of sodium hydride (50% in oil). Ethyl 3-cyano-3-phenylpyruvate (9.55 g., 0.044 mol.) was added in portions at -10° and the reaction mixture was stirred at 25° for 12 hours. The mixture was diluted with 150 ml. of water, extracted with ether, acidified with 15 ml. of acetic acid and the solid was collected by filtration to yield 2-(p-chloro-phenyl)-5-phenyl-3,4-dioxoadiponitrile, m.p. 210° (dec.).

Workup

  1. additionThe mixture was diluted with 150 ml
  2. extractionof water, extracted with ether
  3. filtrationof acetic acid and the solid was collected by filtration

Sources & evidence

ORD record
ord-f5baca5f217343a284bb0cdbf92096cf
Source dataset
uspto-grants-1976_03
Patent number
US03947580

Linked notes

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