Methylamine → 6-bromo-N-methylpyridin-2-amine

Temperature

80 °C

30 g (0.13 mol) of 2,6-dibromopyridine are added to a solution of 225 ml (2.39 mol) of methylamine in ethanol (33% by weight, Aldrich) precooled to 0° C. The reaction is heated at 80° C. with stirring for 20 hours, in a glass system equipped with a manometer. The reaction is monitored by TLC control. The reaction medium is cooled to 0° C. and the assembly is opened. The slightly brown solution thus obtained is concentrated under vacuum to a volume of 60 ml, and water (240 ml) is then added, followed by addition of aqueous sodium carbonate solution (2N, 240 ml). The beige-coloured precipitate formed is filtered off, washed with water and dissolved in dichloromethane (200 ml). The solution is dried over magnesium sulfate and the solvent is evaporated off. The addition of heptane allows the precipitation of 17.5 g (74%) of 6-methylamino-2-bromopyridine in the form of a beige-coloured powder.

1. customprecooled to 0° C
2. customequipped with a manometer
3. temperatureThe reaction medium is cooled to 0° C.
4. customThe slightly brown solution thus obtained
5. concentrationis concentrated under vacuum to a volume of 60 ml, and water (240 ml)
6. additionis then added
7. additionfollowed by addition of aqueous sodium carbonate solution (2N, 240 ml)
8. customThe beige-coloured precipitate formed
9. filtrationis filtered off
10. washwashed with water
11. dissolutiondissolved in dichloromethane (200 ml)
12. dry with materialThe solution is dried over magnesium sulfate
13. customthe solvent is evaporated off
14. additionThe addition of heptane
15. customthe precipitation of 17.5 g (74%) of 6-methylamino-2-bromopyridine in the form of a beige-coloured powder

ORD record

ord-df76d6699a9448ae8ab5cd55fb299c19

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513297B2