8-Hydroxyquinoline → 1,2,3,4-Tetrahydroquinolin-8-ol

HRID 1905391Notes

Reaction equation

HRID 1905391 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>CO.[Pt]=O>[NH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[OH:1])[CH2:7][CH2:8][CH2:9]1

Participants

4

Reactant 1

HCID 19238-Hydroxyquinoline

Product 1

HCID 2414901,2,3,4-Tetrahydroquinolin-8-ol

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A solution of 2.5 g (17.2 mmol) of 8-hydroxyquinoline in 50 ml of methanol was treated with 680 mg of platinum oxide and was hydrogenated in a Parr apparatus at 40 PSI until hydrogen absorption ceased. The suspension was filtered through Celite, the filtrate was evaporated and the residue was recrystallized from dichloromethane: hexane to provide 1.82 g of analytically pure, green tinged needles: melting point 117.5°-119° C.

Workup

  1. customwas hydrogenated in a Parr apparatus at 40 PSI until hydrogen absorption
  2. filtrationThe suspension was filtered through Celite
  3. customthe filtrate was evaporated
  4. customthe residue was recrystallized from dichloromethane
  5. customhexane to provide 1.82 g of analytically pure, green tinged needles

Sources & evidence

ORD record
ord-3f7eb0d5feda4709aabb6372f18ec26f
Source dataset
uspto-grants-1989_06
Patent number
US04843082

Reaction notes

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