Nitrogen → 5-amino-2-benzylisoquinolin-1(2H)-one

HRID 459836Notes

Reaction equation

HRID 459836 reaction equation
[CH2:1]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:18]([O-])=O)[C:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N#N.[H][H]>CCO.[Pd]>[NH2:18][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH:16]=[CH:17][N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]2=[O:21]

Participants

6

Reactant 3

HCID 947NitrogenHCID 184445282-benzyl-5-nitroisoquinolin-1(2H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 184445335-amino-2-benzylisoquinolin-1(2H)-oneYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Benzyl-5-nitro-2H-isoquinolin-1-one (1.0 g, 3.57 mmol) from step 3 was dissolved in 10 mL of EtOH, and a catalytic amount (50 mg) of 10% palladium on charcoal was added (under N2 atmosphere). The vessel was then closed and exposed to hydrogen at 1 atmosphere for 2 hours. TLC indicated that reduction of the nitro group was complete after 1 hour, and the mixture was filtered and concentrated in vacuo to give 5-amino-2-benzyl-2H-isoquinolin-1-one (0.687 g, 2.75 mmol) as a pale yellow solid.

Workup

  1. customThe vessel was then closed
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18c40a997b694875bac7aa2516fc1235
Source dataset
uspto-grants-2007_03
Patent number
US07196088B2

Reaction notes

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