Methanol → (S)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propanamide

HRID 1161197Notes

Reaction equation

HRID 1161197 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]([C@@H:15]([CH3:19])[C:16]([NH2:18])=[O:17])[C:9]2=[O:14])([O-])=O.CO>ClCCl.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]([C@@H:15]([CH3:19])[C:16]([NH2:18])=[O:17])[C:9]2=[O:14]

Participants

5

Reactant 2

HCID 887MethanolHCID 59515862(S)-2-(5-Nitro-1-oxoisoquinolin-2(1H)-yl)propanamide

Product 1

HCID 59515789(S)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide (1.3 g, 0.0050 mol) in methanol (40 mL, 1 mol) and dichloromethane (5 mL) was added palladium on charcoal (0.2 g, 0.001 mol) and stirred under hydrogen (1 atm) for 2 h. The reaction mixture was filtered over celite and the filtrate removed under reduced pressure to yield the pure product as an off white solid. MS m/z=232.5 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. customthe filtrate removed under reduced pressure
  3. customto yield the pure product as an off white solid

Sources & evidence

ORD record
ord-852084b2deca4b4cbab6be8f6936d647
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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