2-Methyl-8-hydroxyquinoline → 2-Methyl-1,2,3,4-tetrahydroquinolin-8-ol

HRID 322012

Reaction equation

HRID 322012 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2>CO.O=[Pt]=O>[CH3:12][CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([OH:1])[CH:3]=[CH:4][CH:5]=2)[NH:10]1

Participants

4

Reactant 1

HCID 132242-Methyl-8-hydroxyquinoline

Product 1

HCID 38227352-Methyl-1,2,3,4-tetrahydroquinolin-8-ol

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

7.50 g (47.0 mmol) of 8-hydroxy-2-methylquinoline were hydrogenated in an autoclave in the presence of 0.75 g of PtO2 in 60 ml of methanol at 4 bar of H2 and a temperature of 50° C. for 24 h. The reaction solution was filtered, and the filtrate was concentrated to dryness. The residue of 2-methyl-8-hydroxy-1,2,3,4-tetrahydroquinoline obtained was dissolved in 60 ml of ethanol, 3.85 ml of 37% strength formaldehyde solution and 1.1 g of Pd/C (10% strength) were added, and the reaction mixture obtained was hydrogenated in an autoclave at 4 bar of H2 and a temperature of 50° C. again for 24 h. It was filtered, the filtrate was concentrated, and the residue was purified by chromatography on SiO2 (EA/n-heptane 1:4). 1.56 g of the title compound were obtained.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-c903ed02a5dc468baf72f8ecc3fdc0d3
Source dataset
uspto-grants-2001_04
Patent number
US06211196B1

Linked notes

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