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

HRID 1161248Notes

Reaction equation

HRID 1161248 reaction equation
[CH:1]1([NH:4][C:5](=[O:22])[C@H:6]([N:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[N+:18]([O-])=O)[C:9]2=[O:21])[CH3:7])[CH2:3][CH2:2]1.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:6]([CH3:7])[C:5]([NH:4][CH:1]1[CH2:3][CH2:2]1)=[O:22])[C:9]2=[O:21]

Participants

4

Reactant 2

HCID 887MethanolHCID 59515780(R)-N-Cyclopropyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide

Product 1

HCID 59515716(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)-N-cyclopropylpropanamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(R)-N-Cyclopropyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide (0.6 g, 0.002 mol) was stirred with palladium 10% wt. on calcium carbonate (0.1 g, 0.00005 mol) in methanol (30 mL, 0.7 mol) under hydrogen (balloon) over 1 h at room temperature. The catalyst was filtered, the filtrate was concentrated to dryness gave a brown solid. MS m/z 271.7 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customgave a brown solid

Sources & evidence

ORD record
ord-f0f57e1c90de42ebb5825b0d0fe347b4
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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