p-Toluenesulfonic acid → 68903-25-3

HRID 1268881Notes

Reaction equation

HRID 1268881 reaction equation
[C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[N+:8]([C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14])([O-:10])=[O:9].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N+:8]([C:11]1[CH:12]=[C:13]([NH:14][C:1]([CH3:2])=[CH:4][C:5](=[O:7])[CH3:6])[CH:15]=[CH:16][CH:17]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 74233-NitroanilineHCID 31261Acetylacetone

Product 1

HCID 274863568903-25-3

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

36.24 g (362 mmol) Acetylacetone, 10.00 g (72 mmol) 3-nitroaniline, and 1.25 g (7.2 mmol) 4-toluenesulfonic acid are dissolved in 100 ml toluene. The reaction mixture is refluxed overnight with a Dean-Stark trap to remove water. After cooling down to room temperature, the solvent is removed in vacuo and the residue is purified by column chromatography on silica with eluent dichloromethane.

Workup

  1. temperatureThe reaction mixture is refluxed overnight with a Dean-Stark trap
  2. customto remove water
  3. customthe solvent is removed in vacuo
  4. customthe residue is purified by column chromatography on silica with eluent dichloromethane

Sources & evidence

ORD record
ord-18773cda42de45bcb57dd13a0e99988e
Source dataset
uspto-grants-2007_04
Patent number
US07199136B2

Reaction notes

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