Carbon Dioxide → 4-Hydroxyquinoline

HRID 2166876Notes

Reaction equation

HRID 2166876 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[C:3](C(O)=O)=[CH:2]1.C(=O)=O.C>C(O)C>[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 297MethaneHCID 2208754-Quinolone-3-carboxylic acid

Product 1

HCID 691414-Hydroxyquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 4(1H)-quinolone-3-carboxylic acid (65.5 g) was stirred and heated in a flask set in a fluidised sand bath at 270° C., under nitrogen, until no more CO2 was evolved (about twenty minutes). The fused mass was allowed to cool and then dissolved in boiling ethanol (400 ml). The solution was treated with charcoal, and filtered. The filtrates were evaporated to dryness, the residue dissolved in boiling n-butanol (80 ml), the solution cooled, and an equal volume of diethyl ether then added. The cream solid was collected and dried to give 4(1H)-quinolone, m.p. 205° C.

Workup

  1. temperatureheated in a flask
  2. custom(about twenty minutes)
  3. temperatureto cool
  4. dissolutiondissolved
  5. filtrationfiltered
  6. customThe filtrates were evaporated to dryness
  7. dissolutionthe residue dissolved
  8. temperaturethe solution cooled
  9. additionan equal volume of diethyl ether then added
  10. customThe cream solid was collected
  11. customdried

Sources & evidence

ORD record
ord-973047eb0ed1471d8fc2cbacc9b56644
Source dataset
uspto-grants-1983_06
Patent number
US04390541

Reaction notes

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