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

HRID 418483Notes

Reaction equation

HRID 418483 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]=[CH:13][C:14]=2[N+:18]([O-])=O)[C:9]1=[O:21])[CH3:7])(=[O:3])[CH3:2].C(O)C.[Cl-].[NH4+].O>[Fe]>[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]=[CH:13][C:14]=2[NH2:18])[C:9]1=[O:21])[CH3:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 59515745(R)-2-(5-Nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 59515825(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propyl acetateYield 100%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Conditions

Temperature
85 °C

Procedure

A round bottom flask was charged with (R)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate (24 g, 0.074 mol), ethanol (500 mL, 8 mol), and was heated at 85° C. Ammonium chloride (50 g, 0.9 mol) in water (150 mL, 8.3 mol) was added followed by iron (20 g, 0.3 mol) in two portions. The reaction was stirred for 1 hour and poured onto dichloromethane (200 mL) and extracted. the solvent was removed under reduced pressureunder reduced pressure to afford the desired product as red oil (19 g, 100%).

Workup

  1. additionpoured onto dichloromethane (200 mL)
  2. extractionextracted
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-13eba42cffa7465dae71fb0bfb98c167
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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