4-Hydroxybenzaldehyde → 1-(p-Carboxyphenyl)-3-methyl-4-(p-hydroxybenzylidene)-2-pyrazolin-5-one

HRID 1106101Notes

Reaction equation

HRID 1106101 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].[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1>CN(C)C=O.CO>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[C:13](=[CH:22][C:21]3[CH:24]=[CH:25][C:18]([OH:17])=[CH:19][CH:20]=3)[C:12]([CH3:16])=[N:11]2)=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 1090294-(3-Methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

Product 1

HCID 7265991-(p-Carboxyphenyl)-3-methyl-4-(p-hydroxybenzylidene)-2-pyrazolin-5-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

218 g (1 mole) of 1-p-carboxyphenyl-3-methyl-2-pyrazolin-5-one were suspended in 600 ml of dimethylformamide. The mixture obtained was heated with stirring to 100° C., whereupon a solution of 122 g (1mole) of p-hydroxybenzaldehyde in 400 ml of methanol was added. The dissolution of both compounds was complete. The dye started crystallizing after some 30 min. The heating was stopped after 2 h and the reaction mixture was allowed to cool down to room temperature. The dye was filtered with suction and rinsed with methanol.

Workup

  1. customThe mixture obtained
  2. temperaturewas heated
  3. additionwas added
  4. dissolutionThe dissolution of both compounds
  5. customThe dye started crystallizing after some 30 min
  6. filtrationThe dye was filtered with suction
  7. washrinsed with methanol

Sources & evidence

ORD record
ord-e29fc5f5b24d4686b2c8b7d7c5423af7
Source dataset
uspto-grants-1982_01
Patent number
US04311787

Reaction notes

Loading…