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

5-Amino-2-(3-aminopropyl)-3-methylpyridine (8.05 g) in hydrobromic acid (48%, 75 ml) and water (8 ml) wasreacted 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 3×150 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.

1. stirringstirred at room temperature for 3 hours
2. customThe cooled reaction mixture
3. extractionwas then extracted with chloroform 3×150 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

ORD record

ord-9465c95b41ee425b9b6a12fd598f2ebc

Source dataset

uspto-grants-1988_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04764519