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

HRID 1161203Notes

Reaction equation

HRID 1161203 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].C(OC(=O)C)C>[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 59515648(R)-2-(5-Nitro-1-oxoisoquinolin-2(1H)-yl)propanamide

Product 1

HCID 59515719(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A round bottom flask was charged with (R)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide (5.0 g, 0.018 mol), palladium on charcoal (10%) (0.3 g, 0.003 mol) and methanol (200 mL, 5 mol) and ethylacetate (80 mL). The reaction mixture was stirred under hydrogen (1 atm) at room temperature for 40 minutes. The mixture was filtered over celite, the solvent was removed to yield the product as a light yellow solid. MS m/z=232.3 (M+H).

Workup

  1. filtrationThe mixture was filtered over celite
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-64195eda6fb0403d95b6686d34fb1398
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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