2-Hydroxyquinoline → Quinoline

HRID 1809344Notes

Reaction equation

HRID 1809344 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]1=O.O1CCOCC1.O=P(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>CCOC(C)=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

6

Reactant 4

HCID 60382-HydroxyquinolineHCID 24813Phosphorus oxychlorideHCID 312751,4-DioxaneHCID 516892Sodium Bicarbonate

Product 1

HCID 7047Quinoline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

In a 100 ml flask was placed starting material quinolone (4.22 g) and dioxane (40 ml). POCl3 (4.6 g) was added, and the mixture was heated to 75° C. After 2 hours, HPLC showed the reaction finished (99.7% conversion). Reaction mixture was cooled to room temperature, and then poured to 100 ml saturated NaHCO3 solution and 20 ml EtOAc. The resulting suspension was stirred for 3 hours. Product was isolated by filtration, washing with EtOAc and drying under vacuum. Yield: 4.0 g, 90.9%.

Workup

  1. customIn a 100 ml flask was placed starting
  2. customReaction mixture
  3. temperaturewas cooled to room temperature
  4. customProduct was isolated by filtration
  5. washwashing with EtOAc
  6. customdrying under vacuum

Sources & evidence

ORD record
ord-5c7ad6e0d2fb49b3b58b2d59d9b328d6
Source dataset
uspto-grants-2013_01
Patent number
US08362035B2

Reaction notes

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