4-(Dimethylamino)Benzaldehyde → (4-(4-(4-Dimethylaminobenzyliden-1-yl)-3-methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

HRID 1381484Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1381484
[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]([CH3:27])[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1>CCO>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[C:13](=[CH:23][C:22]3[CH:25]=[CH:26][C:19]([N:18]([CH3:27])[CH3:17])=[CH:20][CH:21]=3)[C:12]([CH3:16])=[N:11]2)=[CH:8][CH:9]=1)([OH:3])=[O:2]

Komponenten

4

Edukt 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 1090294-(3-Methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

Produkt 1

HCID 776848(4-(4-(4-Dimethylaminobenzyliden-1-yl)-3-methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A slurry composed of 1-(4-carboxyphenyl)-3-methyl-2-pyrazolin-5-one (21.8 gm, 0.10 mol), 4-dimethylaminobenzaldehyde (14.9 gm, 0.10 mol) and EtOH (250 ml) was heated at reflux for two hours. The reaction mixture was cooled to RT resulting in a crude orange product which was isolated by filtration. The product was then washed with ether and dried. The product was purified further by making a slurry of the solid in EtOH (700 ml) at refluxing temperature and filtering the slurry to recover the dye. The treatment was repeated. The mp of the product was above 310° C. The NMR and IR spectra were consistent with the structure assigned. The C,H, and N elemental analyses were in agreement with those calculated for the empirical formula.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for two hours
  3. customresulting in a crude orange product which
  4. customwas isolated by filtration
  5. washThe product was then washed with ether
  6. customdried
  7. customThe product was purified further
  8. temperatureat refluxing temperature
  9. filtrationfiltering the slurry
  10. customto recover the dye
  11. customwas above 310° C

Quellen und Nachweise

ORD-Eintrag
ord-d792f146e30a482c89875bf2a224fc57
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04803150

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