4-(Dimethylamino)Benzaldehyde → HCID 2921369, compound

HRID 1722619Notes

Reaction equation

HRID 1722619 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:13]2[C:17](=[O:18])[CH2:16][C:15]([CH3:19])=[N:14]2)[CH:7]=[C:8]([C:10]([OH:12])=[O:11])[CH:9]=1)([OH:3])=[O:2].[CH3:20][N:21]([CH3:30])[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1>CCO>[C:10]([C:8]1[CH:7]=[C:6]([N:13]2[C:17](=[O:18])[C:16](=[CH:26][C:25]3[CH:28]=[CH:29][C:22]([N:21]([CH3:30])[CH3:20])=[CH:23][CH:24]=3)[C:15]([CH3:19])=[N:14]2)[CH:5]=[C:4]([C:1]([OH:3])=[O:2])[CH:9]=1)([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 14645800HCID 14645800, compound

Product 1

HCID 2921369HCID 2921369, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A slurry composed of 1-(3,5-dicarboxyphenyl)-3-methyl-2-pyrazoline-5-one (44.6 grams, 0.17 mol), 4-dimethylamino-benzaldehyde (26.9 grams, 0.18 mol) and EtOH (500 mL) was heated at reflux for three hours. The reaction mixture was chilled in ice and the resulting crude orange product was isolated by filtration and washed with EtOH (200 mL). The product was purified by three repetitive slurries of the solid in acetone (1.4 l) at reflux and filtering to recover the dye. 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.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for three hours
  3. temperatureThe reaction mixture was chilled in ice
  4. customthe resulting crude orange product was isolated by filtration
  5. washwashed with EtOH (200 mL)
  6. customThe product was purified by three repetitive slurries of the solid in acetone (1.4 l)
  7. temperatureat reflux
  8. filtrationfiltering
  9. customto recover the dye
  10. customwas above 310° C

Sources & evidence

ORD record
ord-0aab666db5494d42b7893501ee56f423
Source dataset
uspto-grants-1989_08
Patent number
US04857446

Reaction notes

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