Methanol → (R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)-N,3-dimethylbutanamide

HRID 1161232Notes

Reaction equation

HRID 1161232 reaction equation
[CH3:1][CH:2]([CH3:22])[C@@H:3]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:18]([O-])=O)[C:9]1=[O:21])[C:4]([NH:6][CH3:7])=[O:5].CO>[Pd]>[NH2:18][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH:16]=[CH:17][N:8]([C@H:3]([CH:2]([CH3:22])[CH3:1])[C:4]([NH:6][CH3:7])=[O:5])[C:9]2=[O:21]

Participants

4

Reactant 2

HCID 887MethanolHCID 59515853(R)-3,N-Dimethyl-2-(5-nitro-1-oxo-1H-isoquinolin-2-yl)-butyramide

Product 1

HCID 59515790(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)-N,3-dimethylbutanamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(R)-3,N-Dimethyl-2-(5-nitro-1-oxo-1H-isoquinolin-2-yl)-butyramide (1.4 g, 0.0045 mol) was stirred with palladium 10% wt. on calcium carbonate (1.4 g, 0.00068 mol) in methanol (100 mL, 2 mol) under hydrogen (balloon) over 1 h at room temperature. The catalyst was filtered, the filtrate was concentrated to dryness to give a yellow solid. MS m/z 273.9 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customto give a yellow solid

Sources & evidence

ORD record
ord-0d833d9d1953449eb55ad26ea2bc6b46
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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