4-Hydroxyquinoline → Quinoline

HRID 1534471Notes

Reaction equation

HRID 1534471 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH:3]=[CH:2]1>P(Cl)(Cl)(Cl)=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 691414-Hydroxyquinoline

Product 1

HCID 7047QuinolineYield 79.4%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

3-butyryl-6-benzoyloxymethyl)-4(1H)-quinolone (30 g) was heated under reflux in phosphorus oxychloride (200 ml) for 30 minutes. The solvent was evaporated and the residue partitioned between dichloromethane and ammonia solution. The organic layer was washed successively with sodium hydrogen carbonate solution and 50% brine. Dried anhyd. MgSO4), filtered and evaporated to an oily solid which crystallized on trituration with petroleum ether to give 3-butyryl-4-chloro-6-benzyloxymethyl)quinoline (21.2 g, 67%), m.p. 85° C.-6° C.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between dichloromethane and ammonia solution
  3. washThe organic layer was washed successively with sodium hydrogen carbonate solution and 50% brine
  4. customDried
  5. filtrationMgSO4), filtered
  6. customevaporated to an oily solid which
  7. customcrystallized on trituration with petroleum ether

Sources & evidence

ORD record
ord-14c173a9bff4469eb6fc04397d1b6174
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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