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

HRID 418504Notes

Reaction equation

HRID 418504 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. The flask was evacuated and flushed with hydrogen two times and the reaction was stirred under hydrogen (1 atm) for 2 hours. The reaction was filtered over celite and the solvent was removed to afford the product.

Workup

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

Sources & evidence

ORD record
ord-92b0d683d2f5487ebe3ee666333173f7
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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