p-Nitroacetophenone → 2-[1-(4-Nitrophenyl)ethylidene]malononitrile

HRID 1159460Notes

Reaction equation

HRID 1159460 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13](#[N:17])[CH2:14][C:15]#[N:16]>C1C=CC=CC=1.C(O)(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[C:14]([C:13]#[N:17])[C:15]#[N:16])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 7487p-NitroacetophenoneHCID 8010Malononitrile

Product 1

HCID 110420862-[1-(4-Nitrophenyl)ethylidene]malononitrileYield 29%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 241BenzeneSolvent

Procedure

A mixture of 1-(4-Nitro-phenyl)ethanone (10 g, 60.5 mmol), malononitrile (4 g, 60.5 mmol), NH4OAc (4.66 g, 121 mmol) in benzene (100 mL) and acetic acid (6.4 mL) was refluxed overnight using a Dean Stark to collect water. The reaction was allowed to cool to r.t., partitioned between water and EtOAc (3×). the combined organic were washed with brine, dried (Na2SO4), concentrated and purified via silica gel chromatography eluting with 3 to 1 hexanes:EtOAc to give 3.71 g (29%) of the title compound. Rf=0.22 (4:1 hexanes: EtOAc).

Workup

  1. temperaturewas refluxed overnight
  2. customto collect water
  3. custompartitioned between water and EtOAc (3×)
  4. washthe combined organic were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified via silica gel chromatography
  8. washeluting with 3 to 1 hexanes

Sources & evidence

ORD record
ord-ef834594c77449b8b77d87806597b522
Source dataset
uspto-grants-2010_10
Patent number
US07812166B2

Reaction notes

Loading…