Benzaldehyde → 3-Carboxy-1-(4-Sulfobenzyl)pyrazoline-5-one

HRID 1762692Notes

Reaction equation

HRID 1762692 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([C:12]1[NH:13][N:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](=[O:17])[CH:16]=1)([OH:11])=[O:10].[S:24](=O)(=[O:27])([OH:26])[OH:25]>C(OCC)(=O)C>[CH2:1]([O:10][C:9]([C:12]1[NH:13][N:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](=[O:17])[CH:16]=1)=[O:11])[CH3:2].[C:9]([C:12]1[NH:13][N:14]([CH2:1][C:2]2[CH:7]=[CH:6][C:5]([S:24]([OH:27])(=[O:26])=[O:25])=[CH:4][CH:3]=2)[C:15](=[O:17])[CH:16]=1)([OH:11])=[O:10]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 1118Sulfuric AcidHCID 91673915-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-3-carboxylic acid

Product 2

HCID 4056539ethyl 5-hydroxy-1-phenyl-1H-pyrazole-3-carboxylateHCID 544272973-Carboxy-1-(4-Sulfobenzyl)pyrazoline-5-oneYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

3-Ethoxycarbonyl-1-phenylpyrazoline-5-one (F-1) was prepared in the same manner as in Synthesis 1-(1), except benzaldehyde was used in place of sodium 2-formylbenzenesulfonate. Further, (F-1) was hydrolyzed by the same method as used in Synthesis 1-(5) to be converted to 3-carboxy-1-phenylpyrazoline-5-one (F-2). 7 g of (F-2) was added to 28 ml of concentrated sulfuric acid and heated at 110° C. for 2 hours. After cooling, 140 ml of ethyl acetate was added to the reaction mixture and allowed to stand overnight to yield 7.8 g (yield: 82%) of Intermediate F. Melting Point: 276° C. (decomposed).

Workup

  1. customas used in Synthesis 1-(5)
  2. temperatureAfter cooling

Sources & evidence

ORD record
ord-64cd46c5b41a456e8658c1f3d494b2f5
Source dataset
uspto-grants-1989_05
Patent number
US04833246

Reaction notes

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