Acetic Acid → 1-(p-Carboxyphenyl)-3-methyl-4-(2'-hydroxy-3'-methoxybenzylidene)-2-pyrazolin-5-one

HRID 1106100Notes

Reaction equation

HRID 1106100 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].O=C[C:19]1[CH:27]=[CH:26][C:23]([O:24][CH3:25])=[C:21]([OH:22])[CH:20]=1.[C:28](O)(=O)C>>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[C:13](=[CH:28][C:20]3[CH:19]=[CH:27][CH:26]=[C:23]([O:24][CH3:25])[C:21]=3[OH:22])[C:12]([CH3:16])=[N:11]2)=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 12127IsovanillinHCID 1090294-(3-Methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

Product 1

HCID 12269481-(p-Carboxyphenyl)-3-methyl-4-(2'-hydroxy-3'-methoxybenzylidene)-2-pyrazolin-5-one

Procedure

218 g (1 mole) of 1-p-carboxyphenyl-3-methyl-2-pyrazolin-5-one and 152 g (1 mole) of iso-vanillin were suspended in 1000 ml of acetic acid and refluxed for 3 h. After cooling down to room temperature the dye was filtered with suction and rinsed with acetone.

Workup

  1. temperaturerefluxed for 3 h
  2. filtrationwas filtered with suction
  3. washrinsed with acetone

Sources & evidence

ORD record
ord-928747c440f14da0b5d43ff7d1667093
Source dataset
uspto-grants-1982_01
Patent number
US04311787

Reaction notes

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