7,8-Dihydro-6H-isoquinolin-5-one oxime → 5,6,7,8-Tetrahydroisoquinolin-5-amine

HRID 2117315Notes

Reaction equation

HRID 2117315 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[N:11]O)[C:5]=2[CH:4]=[CH:3][N:2]=1>C(O)C.C(OCC)(=O)C.[Pd]>[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([NH2:11])[C:5]=2[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 1

HCID 1357421827,8-Dihydro-6H-isoquinolin-5-one oxime

Product 1

HCID 120990625,6,7,8-Tetrahydroisoquinolin-5-amineYield 103.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7,8-dihydroisoquinolin-5-(6H)-one oxime [Synth. Commun., 26(12), 2305-2308, (1996)] (1 g, 6.2 mmol) in ethanol (20 ml) and ethyl acetate (1 ml) was added 10% palladium on carbon (250 mg). The resulting slurry was stirred under a hydrogen balloon at room temperature for 20 hours. The catalyst was removed by filtration and the solvent evaporated to give the title compound as a brown oil (953 mg, 100%). m/z (ES+) 149 (M+H+).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-fe3ee84a4e354d75a2ea03d47974f8a8
Source dataset
uspto-grants-2008_10
Patent number
US07442701B2

Reaction notes

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