Hydrogen Bromide → 2-(3-Aminopropyl)-5-bromo-3-methylpyridine

HRID 1607046

Reaktionsgleichung

Reaktionsgleichung von HRID 1607046
N[C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([CH2:8][CH2:9][CH2:10][NH2:11])=[N:6][CH:7]=1.N([O-])=O.[Na+].[OH-].[NH4+].[BrH:19]>O.[Cu]>[NH2:11][CH2:10][CH2:9][CH2:8][C:5]1[C:4]([CH3:12])=[CH:3][C:2]([Br:19])=[CH:7][N:6]=1

Komponenten

7

Edukt 4

HCID 260Hydrogen BromideHCID 14923Ammonium HydroxideHCID 198517805-Amino-2-(3-aminopropyl)-3-methylpyridineHCID 23668193Sodium Nitrite

Produkt 1

HCID 198517812-(3-Aminopropyl)-5-bromo-3-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

5-Amino-2-(3-aminopropyl)-3-methylpyridine (8.05 g) in hydrobromic acid (48%, 75 ml) and water (8 ml) was reacted with cuprous bromide (8.73 g) and copper bronze (0.29 g). A solution of sodium nitrite (5.1 g) in water (8 ml) was added at 5°-8° C. over 40 minutes, the reaction mixture was allowed to stir at 5°-8° C. for one hour and then stirred at room temperature for 3 hours. The cooled reaction mixture was then basified with ammonium hydroxide (70 ml), which was then extracted with chloroform 3 x 150 ml. The chloroform extracts were then washed with fresh ammonium hydroxide and water (70 ml of each) till no more blue colour was visible in the aqueous layer. Chloroform extracts were dried over magnesium sulphate, filtered and concentrated to dryness to give the title compound (8.2 g) as an amber oil.

Aufarbeitung

  1. stirringstirred at room temperature for 3 hours
  2. customThe cooled reaction mixture
  3. extractionwas then extracted with chloroform 3 x 150 ml
  4. washThe chloroform extracts were then washed with fresh ammonium hydroxide and water (70 ml of each) till no more blue colour
  5. dry with materialChloroform extracts were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-77b88b579d3c4cb0a118398808265d3b
Quelldatensatz
uspto-grants-1989_09
Patentnummer
US04863933

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