Ammonium Chloride → 5-Bromoisoquinolin-8-amine

HRID 1519872

Reaktionsgleichung

Reaktionsgleichung von HRID 1519872
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[Cl-].[NH4+]>CO.[Fe]>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 8169835-Bromo-8-nitroisoquinoline

Produkt 1

HCID 162183025-Bromoisoquinolin-8-amineAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A 3-neck flask was charged with 5-bromo-8-nitroisoquinoline (4 g, 15.8 mmol) and dissolved in MeOH (50 mL). A condenser was affixed and the mixture was heated to 100° C. Aqueous (20 mL) solution of ammonium chloride (4.12 g, 79 mmol) was added slowly, followed by iron powder (3 g, 53.7 mmol). The heterogeneous mixture was stirred at 100° C. for 3 h. LCMS confirmed complete reduction to the amine. The mixture was filtered and the solution was concentrated under reduced pressure to give a brown solid as crude product (2.4 g, 68%). LCMS showed an m/z of 225.0/223.0 with a retention time of 0.767 min, method [1].

Aufarbeitung

  1. customA condenser was affixed
  2. filtrationThe mixture was filtered
  3. concentrationthe solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0e21818536cd4db3bdca9e99f9c80743
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073891B2

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