Ethanol → (R)-2-(5-Amino-6-cyclopropyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 1161281Notes

Reaction equation

HRID 1161281 reaction equation
[C:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:21]3[CH2:23][CH2:22]3)[C:14]=2[N+:18]([O-])=O)[C:9]1=[O:24])[CH3:7])(=[O:3])[CH3:2].C(O)C>[Pd]>[C:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:21]3[CH2:22][CH2:23]3)[C:14]=2[NH2:18])[C:9]1=[O:24])[CH3:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 59515735(R)-2-(6-Cyclopropyl-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 59515874(R)-2-(5-Amino-6-cyclopropyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A round bottom flask was charged with (R)-2-(6-cyclopropyl-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate (28 mg, 0.000085 mol), ethanol (10 mL, 0.2 mol) and palladium, 10% weight on charcoal (1.0 mg, 0.0000085 mol) was added and the flask was evacuated of any air and flushed with hydrogen two times and the reaction was stirred at room temperature under hydrogen (1 atm) for 2 hours. The reaction was filtered over celite and the solvent removed to obtain the product. MS m/z=301.2 (M+H).

Workup

  1. additionwas added
  2. customthe flask was evacuated of any air
  3. customflushed with hydrogen two times
  4. filtrationThe reaction was filtered over celite
  5. customthe solvent removed
  6. customto obtain the product

Sources & evidence

ORD record
ord-9f87864a7d484e4c99af61e6ba7c4e25
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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