Dimethylformamide → N-[6-(aminomethyl)-1-isoquinolinyl]benzamide

HRID 636963Notes

Reaction equation

HRID 636963 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([NH:15][C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[N:10][CH:9]=[CH:8]2)=[N+]=[N-].CN(C)C=O>C(O)C.[Pd]>[NH2:1][CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([NH:15][C:16](=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[N:10][CH:9]=[CH:8]2

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 22665816N-[6-(azidomethyl)-1-isoquinolinyl]benzamide

Product 1

HCID 22665809N-[6-(aminomethyl)-1-isoquinolinyl]benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 6.4 g of N-[6-(azidomethyl)-1-isoquinolinyl]benzamide in 300 mL of ethanol and 60 mL of N,N-dimethylformamide containing 3.8 g of 5% palladium/calcium carbonate was hydrogenated for 20 hours. Filtration and concentration i. vac. yielded the title compound as an oil. MS (m/e)=277.

Workup

  1. filtrationFiltration and concentration i

Sources & evidence

ORD record
ord-692633a7bff94325a4fc19e117cc149b
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Reaction notes

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