4-Nitrobenzaldehyde → 2-(4-(Hydroxy(oxido)amino)benzylidene)malononitrile

HRID 1587991Notes

Reaction equation

HRID 1587991 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12](#[N:16])[CH2:13][C:14]#[N:15].C(N(CC)CC)C>C(O)C>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[C:13]([C:12]#[N:16])[C:14]#[N:15])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 8010MalononitrileHCID 8471Triethylamine

Product 1

HCID 20412-(4-(Hydroxy(oxido)amino)benzylidene)malononitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.45 Grams(22.83 mmol) of 4-nitrobenzaldehyde and 1.52 grams(23.03 mmol) of malononitrile were dissolved in 200 milliliters of anhydrous ethanol. To this was added 0.35 milliliter of triethylamine, and the mixture was stirred and refluxed, under nitrogen, for 2 hours. The solvent was removed using a rotary evaporator and the crude reaction product was crystallized from ethanol. 2.33 Grams(51.5%) of the product was obtained. IR (in nujol) analysis showed bands at 3100, 3025, 2950-2850, 2220 (CN), 1595, 1570, 1510, 1450, 1410, 1365, 1340, 1315, 1300, 1210, 935, 850, 835, 780, 745, 680 and 620 cm-1NMR (CDCl3) analysis showed signals at 8.40(d, 2H, J=9 Hz), 8.08(d, 2H, J=9 Hz) and 7.89(s, 1H) ppm.

Workup

  1. temperaturerefluxed, under nitrogen, for 2 hours
  2. customThe solvent was removed
  3. customa rotary evaporator
  4. customthe crude reaction product
  5. customwas crystallized from ethanol
  6. custom2.33 Grams(51.5%) of the product was obtained

Sources & evidence

ORD record
ord-172dfd99787249129f003fe9b281fd17
Source dataset
uspto-grants-1993_06
Patent number
US05220000

Reaction notes

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