7-Prop-2-enylquinolin-8-ol → 8-Hydroxy-7-propylquinoline

HRID 918217Notes

Reaction equation

HRID 918217 reaction equation
[CH2:1]([C:4]1[C:13]([OH:14])=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)[CH:2]=[CH2:3].[H][H]>[Pd].CO>[CH2:1]([C:4]1[C:13]([OH:14])=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 36549187-Prop-2-enylquinolin-8-olHCID 178418361HCID 178418361, compound

Product 1

HCID 116045138-Hydroxy-7-propylquinolineYield 84.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a stainless steel autoclave, one introduces 93 g of 7-allyl-8-hydroxyquinoline (i.e. 0.5 mole), 250 ml of methanol, and 3 g of 5% palladium on charcoal. The hydrogenation is carried out under a 4 kg/cm2 hydrogen pressure. After absorption of a sufficient quantity of hydrogen and cooling, one filters off the catalyst, removes the solvent by distillation under normal pressure, and then distills the residue under high vacuum. The 7-propyl-8-hydroxyquinoline distills at 105°-106°C at a pressure of 0.25 mm Hg. One collects 78 g of a light yellow liquid. Yield = 84.5%.

Workup

  1. customAfter absorption of a sufficient quantity of hydrogen
  2. temperaturecooling
  3. customone filters off the catalyst, removes the solvent
  4. distillationby distillation under normal pressure
  5. distillationdistills the residue under high vacuum
  6. distillationThe 7-propyl-8-hydroxyquinoline distills at 105°-106°C at a pressure of 0.25 mm Hg

Sources & evidence

ORD record
ord-3ebd65f1f6444e99a255d57f76dfe7ec
Source dataset
uspto-grants-1976_07
Patent number
US03970454

Reaction notes

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