6-Methoxyquinoline → Quinoline, 1,2,3,4-tetrahydro-6-methoxy-

HRID 371753

Reaction equation

HRID 371753 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7][CH2:6]2

Participants

4

Reactant 1

HCID 148606-Methoxyquinoline

Product 1

HCID 67113Quinoline, 1,2,3,4-tetrahydro-6-methoxy-Yield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-Methoxyquinoline (1.00g) was dissolved in absolute ethanol (20 ml) and hydrogenated under pressure in the presence of 10% palladium on charcoal (0.10g) with shaking for about 40 hours. Filtration and evaporation to dryness of the filtrate gave 1,2,3,4-tetrahydro-6-methoxyquinoline as a light-brown gum (0.97g). The structure was supported by nmr spectrum.

Workup

  1. filtrationFiltration and evaporation to dryness of the filtrate

Sources & evidence

ORD record
ord-1d27416b936e4f4b9c7fc294a512a2d7
Source dataset
uspto-grants-1978_05
Patent number
US04087561

Linked notes

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