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

HRID 418500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418500
[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]([Cl: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]([Cl:21])[C:14]=2[NH2:18])[C:9]1=[O:22])[CH3:7])(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 59515821(R)-2-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Produkt 1

HCID 59515650(R)-2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23925IronKatalysator

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A round bottom flask was charged with (R)-2-(6-chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate (160.0 mg, 0.0004927 mol) and ethanol (7 mL, 0.1 mol), and the reaction was heated at 85° C. Ammonium chloride (264 mg, 0.00493 mol) in water (7 mL, 0.4 mol) was added, followed by iron (110 mg, 0.0020 mol) in two portions. The reaction was stirred at that temperature for one hour. The reaction mixture was then poured onto dichloromethane (60 mL) and extracted. The extracts were washed with brine, dried, and the solvent removed under reduced pressure to afford the product as a colorless solid.

Aufarbeitung

  1. additionThe reaction mixture was then poured onto dichloromethane (60 mL)
  2. extractionextracted
  3. washThe extracts were washed with brine
  4. customdried
  5. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-845fff6223c84a5eaf0abe5b5e5e0bec
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093265B2

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