1-Chloro-6-methoxy-4-phenylisoquinoline-3-carbonitrile → HCID 68515191, compound

HRID 639873Notes

Reaction equation

HRID 639873 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([C:20]#[N:21])[N:3]=1>CCO.[NH4+].[OH-].[Ni]>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH:2]=[N:3][C:4]([CH2:20][NH2:21])=[C:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 1

HCID 114264141-Chloro-6-methoxy-4-phenylisoquinoline-3-carbonitrile

Product 1

HCID 68515191HCID 68515191, compoundYield 63.2%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of 1-chloro-6-methoxy-4-phenylisoquinoline-3-carbonitrile (150 mg) in 20 mL absolute EtOH and 5 ml aqueous NH4OH was added 150 mg of Raney Ni. The reaction was shaken under 12 (40 psi) for 18 h. Filtration and concentration of the reaction gave 85 mg of 1-(6-methoxy-4-phenylisoquinolin-3-yl)methanamine.

Workup

  1. filtrationFiltration and concentration of the reaction

Sources & evidence

ORD record
ord-8d198a458a5e492499d87db898c82e9b
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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