Methanol → (R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)-N-cyclopropyl-3-methylbutanamide

HRID 1161242Notes

Reaction equation

HRID 1161242 reaction equation
[CH:1]1([NH:4][C:5](=[O:24])[C@H:6]([N:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[N+:20]([O-])=O)[C:11]2=[O:23])[CH:7]([CH3:9])[CH3:8])[CH2:3][CH2:2]1.CO>[Pd]>[NH2:20][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[CH:18]=[CH:19][N:10]([C@H:6]([CH:7]([CH3:9])[CH3:8])[C:5]([NH:4][CH:1]1[CH2:3][CH2:2]1)=[O:24])[C:11]2=[O:23]

Participants

4

Reactant 2

HCID 887MethanolHCID 59515890(R)-N-Cyclopropyl-3-methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)butanamide

Product 1

HCID 59515785(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)-N-cyclopropyl-3-methylbutanamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(R)-N-Cyclopropyl-3-methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)butanamide (1.3 g, 0.0039 mol) was stirred with palladium 10% wt. on calcium carbonate (0.2 g, 0.0001 mol) in methanol (60 mL, 1 mol) under hydrogen (balloon) for 1 h at room temperature. The catalyst was filtered and the filtrate was concentrated to dryness to give a brown oil. MS m/z 301.1 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-02b399ba504449459ec76bb5a5bf8bf3
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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