5-BROMO-2-HYDROXY-3-PICOLINE

Chemical Properties

Uses

Synthesis

3430-21-5

89488-30-2

The general procedure for the synthesis of 5-bromo-3-methylpyridin-2-one from 2-amino-3-methyl-5-bromopyridine is as follows: Example 1. 1A. To a solution of 2.6 M H2SO4 (70 mL) of 2-amino-5-bromo-3-methylpyridine (5.0 g, 26.7 mmol) was added dropwise an aqueous solution (10 mL) of sodium 2-nitrite (5.0 g, 72.5 mmol) at 0 °C. 1B. The reaction mixture was slowly warmed to room temperature and stirring was continued for 1.5 hours. 1C. Upon completion of the reaction, the mixture was filtered and the resulting solid was washed with cold water. 1D. The washed solid was dissolved in dichloromethane (100 mL), dried by adding anhydrous magnesium sulfate, and the solvent was subsequently concentrated to give 5-bromo-3-methylpyridin-2-one (4.2 g, 84% yield). MS (DCI/NH3) m/z: 188/190 (M+H)+.

References