Methylamine → 3-(Aminomethyl)-5-bromopyridine

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Reaction Steps

5-Bromo-3-(phthalimidomethyl)pyridine (7.9 g, 25 mmol) is then hydrolyzed by treatment with aqueous methylamine (40%, 50 mL) and refluxing the mixture for 3 h. The solvents were removed by rotary evaporation to yield a pale yellow-colored solid, which was then taken up into concentrated hydrochloric acid (50 mL) and refluxed for 15 h. The reaction mixture was basified (pH=10–11) with aqueous sodium hydroxide (50%), extracted with chloroform (5×40 mL) and dried (K2CO3). The solvent was removed by rotary evaporation and the product purified by column chromatography to yield (5-bromo-3-pyridyl)methylamine (2.80 g, 59.8% yield).

Provenance & Evidence