Ethanol → 2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)ethyl acetate

HRID 418512Notes

Reaction equation

HRID 418512 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:20])[C:13]=2[N+:17]([O-])=O)[C:8]1=[O:21])(=[O:3])[CH3:2].C(O)C.[Cl-].[NH4+].O>[Fe]>[C:1]([O:4][CH2:5][CH2:6][N:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:20])[C:13]=2[NH2:17])[C:8]1=[O:21])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 595159062-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)ethyl acetate

Product 1

HCID 595156762-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)ethyl acetate

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

A round bottom flask was charged with 2-(6-chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)ethyl acetate (450.00 mg, 0.0014484 mol), ethanol (20 mL, 0.3 mol), and ammonium chloride (774.8 mg, 0.01448 mol) in water (10 mL, 0.6 mol) was added at 85° C., followed by iron (324 mg, 0.00579 mol) in two portions. The reaction was stirred at that temperature for 45 minutes and then poured onto methylene chloride (200 mL) and extracted. The solvent was removed under reduced pressure to afford the pure product as a light yellow solid.

Workup

  1. additionwas added at 85° C.
  2. additionpoured onto methylene chloride (200 mL)
  3. extractionextracted
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-400db91c1c5645b9a0408d55d5d8b875
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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