p-Toluenesulfonic acid → HCID 12803568, compound

HRID 1461961Notes

Reaction equation

HRID 1461961 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([CH:15]=1)[NH:7][C:8](=[O:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:17]1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([CH:15]=1)[NH:7][C:8](=[O:14])[C:9]([O:11][CH:12]([CH3:17])[CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 12803542HCID 12803542, compound

Product 1

HCID 12803568HCID 12803568, compoundYield 735.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2 g of ethyl 5-chloro-2-hydroxyoxanilate, 100 ml of isopropyl alcohol, and 100 mg of p-toluenesulfonic acid was refluxed for 24 hours. The reaction mixture was allowed to cool to room temperature and then allowed to stand overnight. Crystals formed were recovered by filtration and recrystallized from isopropyl alcohol to provide 1.1 g of isopropyl 5-chloro-2-hydroxyoxanilate.

Workup

  1. temperaturewas refluxed for 24 hours
  2. customCrystals formed
  3. filtrationwere recovered by filtration
  4. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-7efb0909fd8a4a3abb95cf0451fb1509
Source dataset
uspto-grants-1984_07
Patent number
US04457872

Reaction notes

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