Sodium Hydroxide → 5-Bromoisoquinoline

HRID 1422163

Reaktionsgleichung

Reaktionsgleichung von HRID 1422163
N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.N([O-])=O.[Na+].[OH-].[Na+].[BrH:18].O>O>[Br:18][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 707665-AminoisoquinolineHCID 22326455Hydrobromide monohydrate2×HCID 23668193Sodium Nitrite

Produkt 1

HCID 7364875-Bromoisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a cold (0° C.) solution of HBr-H2O (48%) (10 ml) in water (30 ml) was added 5-aminoisoquinoline (5 g; 35 mmol) followed by sodium nitrite (2.4 g; 35 mmol) in water (20 ml). The mixture was added to a warm (75° C.) solution of cuprous bromide (5 g; 35 mmol) in HBr-H2O (48%) (50 ml) and stirred overnight at 75° C. The reaction mixture was cooled, basified to pH11 with NaOH (5 M) and steamed distilled to afford the title compound (1.4 g) as a colourless crystalline solid (mp 65° C.).

Aufarbeitung

  1. additionThe mixture was added to
  2. temperatureThe reaction mixture was cooled
  3. distillationsteamed distilled

Quellen und Nachweise

ORD-Eintrag
ord-09106672b3774edca067e001e238bcb2
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06080790

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