4-Hydrazinobenzoic acid → 4-(3,5-dimethyl-1H-pyrazol-1-yl)benzoic acid

HRID 736497Notes

Reaction equation

HRID 736497 reaction equation
[NH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)[NH2:2].[C:12]([CH2:15][C:16](=O)[CH3:17])(=O)[CH3:13]>C(O)C>[CH3:13][C:12]1[CH:15]=[C:16]([CH3:17])[N:1]([C:3]2[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=2)[N:2]=1

Participants

4

Reactant 2

HCID 120894-Hydrazinobenzoic acidHCID 31261Acetylacetone

Product 1

HCID 6932064-(3,5-dimethyl-1H-pyrazol-1-yl)benzoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-hydrazino-benzoic acid (0.60 g, 3.95 mmol) and acetyl acetone (0.405 ml, 3.95 mmol) in ethanol (20 ml) refluxed for 1 hour. Ethanol was removed in vacuum and the remaining solid was triturated with water and collected by filtration to produce 285 (0.71 mg, 83% yield). [M−1]− 215.1.

Workup

  1. customEthanol was removed in vacuum
  2. customthe remaining solid was triturated with water
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-467fcd7a50164796b1aaf9209e41bfb9
Source dataset
uspto-grants-2009_09
Patent number
US07595343B2

Reaction notes

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