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

HRID 1106102Notes

Reaction equation

HRID 1106102 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].[CH:17]1[CH:18]=[CH:19][C:20]([OH:25])=[C:21]([CH:23]=O)[CH:22]=1>C(O)(=O)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[C:13](=[CH:23][C:21]3[CH:22]=[CH:17][CH:18]=[CH:19][C:20]=3[OH:25])[C:12]([CH3:16])=[N:11]2)=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 6998SalicylaldehydeHCID 1090294-(3-Methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

Product 1

HCID 1362771561-(p-Carboxyphenyl)-3-methyl-4-(o-hydroxybenzylidene)-2-pyrazolin-5-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

218 g (1 mole) of 1-p-carboxyphenyl-3-methyl-2-pyrazolin-5-one were suspended in 1000 ml of acetic acid. The suspension was heated to boiling temperature and 112 g (1 mole) of salicyladehyde were added. In the resulting solution the dye started crystallizing very quickly. After 2 h of refluxing the reaction mixture was cooled to room temperature. The dye was filtered with suction and rinsed with acetone.

Workup

  1. temperatureThe suspension was heated
  2. additionwere added
  3. customIn the resulting solution the dye started crystallizing very quickly
  4. temperatureAfter 2 h of refluxing the reaction mixture
  5. filtrationThe dye was filtered with suction
  6. washrinsed with acetone

Sources & evidence

ORD record
ord-a7c35749629a4dd988f5dbf3c860fedc
Source dataset
uspto-grants-1982_01
Patent number
US04311787

Reaction notes

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