Dimethylamine → 6-Bromo-N,N,4-trimethylquinolin-2-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 0.26 g (0.00101 mole) of 6-bromo-2-chloro-4-methylquinoline in 50 ml absolute ethanol was placed in a glass bomb liner, cooled to -78° C., and 7.19 g (0.159 mole) of dimethylamine bubbled into the cold ethanolic solution. The mixture was heated to 112° in a sealed autoclave for 3 hours. The solvent and excess dimethylamine were then removed under vacuum, to leave 0.36 g of residue, which was washed with 40 ml H2O to remove the (CH3)2NH.HCl. The product was then taken up in 40 ml absolute ethanol, treated with Norite A alkaline decolourising carbon and filtered through Celite followed by concentration and addition of 7 ml H2O to induce crystallisation after chilling, the product collected was a light yellow crystalline solid, 0.20 g (74.3%), m.p. 81.9°-84.1° C., and Rf 0.11 on silica with 1:1 CH2Cl2 :hexane.

Provenance & Evidence