Hydrogen Bromide → 2-Amino-5-bromo-4-methylpyridine

Participants

Reaction Conditions

Reaction Steps

2-Amino-4-methylpyridine (110 g, 1.02 mol) in hydrobromic acid (1 L, 48%) was stirred at 70° C. and a solution of hydrogen peroxide (300 mL, 15%) was added dropwise over a one h at such a rate that the temperature of the reaction mixture remained at 70-80° C. The mixture was stirred for 90 min at 70° C. and poured onto crushed ice. The pH was adjusted to 4-5 with sodium carbonate and the precipitated solid (containing mostly dibrominated products) was filtered off and discarded. The pH was subsequently raised to 9 and the precipitated product collected by filtration. Recrystallization from toluene gave 2-Amino-5-bromo-4-methylpyridine (76.3 g, 40%).

Provenance & Evidence