2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-5-nitroisoquinolin-1(2H)-one → 5-Amino-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)isoquinolin-1(2H)-one

HRID 1037778Notes

Reaction equation

HRID 1037778 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][N:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[N+:20]([O-])=O)[C:11]2=[O:23])=[CH:5][CH:4]=1>[Pd].CO>[NH2:20][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[CH:18]=[CH:19][N:10]([CH2:9][C:6]1[CH:7]=[N:8][C:3]([C:2]([F:25])([F:24])[F:1])=[CH:4][CH:5]=1)[C:11]2=[O:23]

Participants

4

Reactant 1

HCID 687695432-((6-(trifluoromethyl)pyridin-3-yl)methyl)-5-nitroisoquinolin-1(2H)-one

Product 1

HCID 687691315-Amino-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)isoquinolin-1(2H)-oneYield 82.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on charcoal (10%) was added to the solution of 2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-5-nitroisoquinolin-1(2H)-one (1.16 g, 0.00315 mol) in methanol (30 mL) and the mixture was stirred under an atmosphere of hydrogen for 40 min. The mixture was filtered through celite. The filterate was concentrated and the residue was purified by column to obtain the product as a beige solid (0.83 g). MS m/z=320.3 (M+H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationThe filterate was concentrated
  3. customthe residue was purified by column

Sources & evidence

ORD record
ord-008085f04ed74b239f27909b37b1b8b2
Source dataset
uspto-grants-2013_10
Patent number
US08546579B2

Reaction notes

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