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

HRID 1161295Notes

Reaction equation

HRID 1161295 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(Cl)Cl>[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

7

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 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent

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 into methylene chloride (200 mL) and extracted. The solvent was removed to give the pure product as a light yellow solid. MS m/z=281.3 (M+H)

Workup

  1. additionwas added at 85° C.
  2. extractionextracted
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-3b141c89002d4c47a1b2b8eee96c1bbe
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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