Hydrochloric Acid → (4-Bromopyridin-2-yl)methanamine

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A solution of 18.70 g of 4-bromopyridine-2-carbonitrile [62150-45-2] in 200 ml of tetrahydrofuran is admixed under argon dropwise with 500 ml of 1M borane-tetrahydrofuran complex solution. The reaction solution is subsequently left to stand at room temperature for 16 hours. The reaction solution is cooled to 0° C., admixed dropwise with 500 ml of 2M HCl and heated to reflux for 30 minutes. The reaction solution is cooled to room temperature, basified with 2M NaOH, saturated with sodium chloride and extracted with tetrahydrofuran (3×300 ml). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F).

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