Acetic Acid → 2-[1-(4-Nitrophenyl)ethylidene]malononitrile

HRID 227608Notes

Reaction equation

HRID 227608 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].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1C=CC=CC=1.O>[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

7

Reactant 4

HCID 176Acetic AcidHCID 7487p-NitroacetophenoneHCID 8010MalononitrileHCID 517165Ammonium Acetate

Product 1

HCID 110420862-[1-(4-Nitrophenyl)ethylidene]malononitrileYield 48.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 1-(4-nitrophenyl)ethanone (15 g, 90.8 mmol), malononitrile (6 g, 90.8 mmol), ammonium acetate (7 g, 90.8 mmol) and acetic acid (10 mL) in benzene (200 mL) was stirred at reflux overnight in a flask equipped with a Dean-Stark trap. The reaction mixture was cooled to room temperature, poured into water, and extracted three times with ethyl acetate. The combined organic extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 25% ethyl acetate/hexanes to provide 9.42 g of the desired product. Rf=0.33 (25% ethyl acetate/hexanes).

Workup

  1. temperatureat reflux overnight in a flask
  2. customequipped with a Dean-Stark trap
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-bd1a019f50e3463480e2a636828d3f82
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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