Ethanol → (R)-2-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 418487Notes

Reaction equation

HRID 418487 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]([CH3:21])[C:14]=2[N+:18]([O-])=O)[C:9]1=[O:22])[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]=[C:13]([CH3:21])[C:14]=2[NH2:18])[C:9]1=[O:22])[CH3:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 59515707(R)-2-(6-Methyl-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 59515683(R)-2-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Conditions

Temperature
85 °C

Procedure

A round bottom flask was charged with (R)-2-(6-methyl-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate (3.4 g, 0.010 mol), ethanol (60 mL, 1 mol), and the solution was heated at 85° C. Ammonium chloride (6 g, 0.1 mol) in water (15 mL, 0.83 mol) was added followed by iron (2 g, 0.04 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 and the residue was purified by flash chromatography to afford the desired product as a light yellow oil.

Workup

  1. additionpoured onto dichloromethane (200 mL)
  2. extractionextracted
  3. customthe solvent was removed
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c9d162ab0d3f4fb4b97570a8c3085fd3
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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