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

HRID 1161200Notes

Reaction equation

HRID 1161200 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>[Pd].ClCCl>[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

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

Workup

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

Sources & evidence

ORD record
ord-a453a90276da4f6cb8b83da4d55dfabe
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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