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

HRID 1161218Notes

Reaction equation

HRID 1161218 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].CCOC(C)=O>[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

Into a round bottom flask was combined (R)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide (5.0 g, 0.018 mol), palladium on C (0.3 g, 0.003 mol) and methanol (200 mL, 5 mol) (about 80 mL EtOAc was added to dissolve the reactants). The reaction mixture was stirred under hydrogen balloon at room temperature for 40 min. The mixture was filtered over celite, MeOH was removed and a solid was obtained (4.02 g). MS m/z=232.4 (M+1).

Workup

  1. customInto a round bottom flask was combined
  2. dissolutionto dissolve the reactants)
  3. filtrationThe mixture was filtered over celite, MeOH
  4. customwas removed
  5. customa solid was obtained (4.02 g)

Sources & evidence

ORD record
ord-ee2380f8ee1148fa91a35ce668e1d8e3
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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