Acetic Acid → 1-(4-Carboxyphenyl)-4-(4-dimethylaminocinnamylidene)-3-methyl-2-pyrazolin-5-one

HRID 1722621Notes

Reaction equation

HRID 1722621 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[CH2:13][C:12]([CH3:16])=[N:11]2)=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH3:17][N:18]([CH3:29])[C:19]1[CH:28]=[CH:27][C:22]([CH:23]=[CH:24][CH:25]=O)=[CH:21][CH:20]=1.C(O)(=O)C>CCO>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[C:13](=[CH:25][CH:24]=[CH:23][C:22]3[CH:21]=[CH:20][C:19]([N:18]([CH3:29])[CH3:17])=[CH:28][CH:27]=3)[C:12]([CH3:16])=[N:11]2)=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 922244-(Dimethylamino)-cinnamaldehydeHCID 1090294-(3-Methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

Product 1

HCID 589660201-(4-Carboxyphenyl)-4-(4-dimethylaminocinnamylidene)-3-methyl-2-pyrazolin-5-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-(4-Carboxyphenyl)-3-methyl-2-pyrazolin-5-one (2.18 g, 0.010 mol), 4-dimethylamino-cinnamaldehyde (1.75 g, 0.010 mol) and glacial acetic acid (10 ml) were mixed together to form a slurry. It was heated to reflux with stirring, held at reflux for five minutes and then cooled to room temperature. EtOH (20 ml) was added to the reaction mixture, which was heated again to reflux, held there for five minutes, and cooled to room temperature. The product was isolated by filtration, washed in succession with ethanol and ligroin, and dried. The reaction was repeated twice on the same scale and the products obtained were all combined. They were treated further by first slurrying in refluxing EtOH (150 ml), isolating the solid by filtration while hot, and then slurrying in refluxing MeOH (200 ml) and isolating it again, while hot, by filtration. The mp was 282°-284° C. The NMR and IR spectra were consistent for the structure assigned. The C, H, and N elemental analyses were in agreement with those calculated for the empirical formula of the dye.

Workup

  1. customto form a slurry
  2. temperatureIt was heated
  3. temperatureto reflux
  4. temperatureat reflux for five minutes
  5. temperaturewas heated again
  6. temperatureto reflux
  7. temperaturecooled to room temperature
  8. customThe product was isolated by filtration
  9. washwashed in succession with ethanol and ligroin
  10. customdried
  11. customthe products obtained
  12. additionThey were treated further by first slurrying
  13. customisolating the solid
  14. filtrationby filtration while hot, and
  15. temperaturein refluxing MeOH (200 ml)
  16. customisolating it again
  17. filtrationwhile hot, by filtration

Sources & evidence

ORD record
ord-fb2ebc91250e4f5d93d94736c21984af
Source dataset
uspto-grants-1989_08
Patent number
US04857446

Reaction notes

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