Acetic Acid → N-ethyl-5-bromo-8-nitrotetrahydroisoquinoline

HRID 48209

Reaktionsgleichung

Reaktionsgleichung von HRID 48209
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[BH4-].[Na+].[C:17](O)(=O)[CH3:18]>C1COCC1>[CH2:17]([N:6]1[CH2:5][CH2:4][CH:3]2[C:8](=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][CH:2]2[Br:1])[CH2:7]1)[CH3:18]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 8169835-Bromo-8-nitroisoquinolineHCID 4311764Sodium borohydride2×

Produkt 1

HCID 69895026N-ethyl-5-bromo-8-nitrotetrahydroisoquinolineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 5-bromo-8-nitroisoquinoline (1 g, 3.95 mmol) in 20 mL THF was cooled to 0° C. and treated sequentially with sodium borohydride (0.75 g, 19.83 mmol) followed by the slow addition of acetic acid (20 mL). The reaction mixture was allowed to warm to room temperature, and an additional 2 equiv. of sodium borohydride was added. After quenching with water and treatment with sodium hydroxide solution to make basic, the reaction mixture was extracted with ethyl acetate. The organic residue was chromatographed on silica gel (25% ethyl acetate in hexane) to give the N-ethyl-5-bromo-8-nitrotetrahydroisoquinoline (0.8 g, 70% yield).

Aufarbeitung

  1. customAfter quenching with water and treatment with sodium hydroxide solution
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. customThe organic residue was chromatographed on silica gel (25% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-14bfbef9101f44bfbc8c35dd9bfd29e6
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703391B2

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