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

HRID 1161285Notes

Reaction equation

HRID 1161285 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(Cl)Cl>[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

7

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 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent

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 (110.0 mg, 0.0003615 mol), ethanol (10 mL, 0.2 mol) and the reaction heated at 85° C. and ammonium chloride (193.4 mg, 0.003615 mol) in water (2 mL, 0.1 mol) was added followed by iron (80.7 mg, 0.00144 mol) in two portions and continued to heat for 30 minutes. The reaction went to completion and was poured into DCM (50 mL) and extracted. The removal of the solvent under reduced pressure gave the pure product as an oil. MS m/z=275.4 (M+H).

Workup

  1. temperatureto heat for 30 minutes
  2. extractionextracted
  3. customThe removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-7061f712081241f69aeb88eb132d76b7
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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