8-Hydroxyquinoline → HCID 178526126, compound

HRID 1490036Notes

Reaction equation

HRID 1490036 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[K+].C([O:15][C:16]([S-])=[S:17])C>CCO>[C:16]([C:3]1[C:2]([OH:1])=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1)([OH:15])=[S:17]

Participants

4

Reactant 2

HCID 19238-HydroxyquinolineHCID 2735045Potassium ethylxanthate

Product 1

HCID 178526126HCID 178526126, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 8-hydroxyquinoline (0.055 mol, 8.0 g) and O-ethylxanthic acid potassium salt (0.056 mol, 9.0 g) in abs. EtOH (20 mL) was placed in a pressure reactor and heated at 160° C. for 40 hours. After cooling, the reaction mixture was washed with a small amount of EtOH. The insoluble material was filtered off and treated with aqueous hydrochloric acid. The insoluble thioacid was separated by filtration and purified by heating with barium carbonate in water. The mixture was filtered off, the filtrate was acidified with hydrochloric acid, and precipitate was collected by filtration to give 7-thiocarboxy-8-hydroxyquinoline (2.61 g) in 18.4% yield.

Workup

  1. temperatureAfter cooling
  2. washthe reaction mixture was washed with a small amount of EtOH
  3. filtrationThe insoluble material was filtered off
  4. additiontreated with aqueous hydrochloric acid
  5. customThe insoluble thioacid was separated by filtration
  6. custompurified
  7. temperatureby heating with barium carbonate in water
  8. filtrationThe mixture was filtered off
  9. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-5c5ee84c32d6475dac9ce43b36588bdc
Source dataset
uspto-grants-1997_10
Patent number
US05681832

Reaction notes

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