Ammonia → 5-(Aminomethyl)-2-chloropyridine

Temperature

80 °C

A stainless steel autoclave was charged with 14.99 g of 2-chloro-5-(chloromethyl)pyridine, 63.01 g of 25% aqueous ammonia and 60 ml of acetonitrile and the mixture was stirred on an oil bath at 80° C. for 2 hours. The reaction mixture was diluted with 12.3 g of 30% aqueous sodium hydroxide solution and concentrated. The residue was diluted with 200 ml of ethanol, dried over anhydrous magnesium sulfate and filtered to remove the insolubles. Finally, the filtrate was concentrated and purified by column chromatography (eluent: dichloromethane-methanol (4:1)) to give 7.66 g of 5-(aminomethyl)-2-chloropyridine as a yellow solid.

1. concentrationconcentrated
2. additionThe residue was diluted with 200 ml of ethanol
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationfiltered
5. customto remove the insolubles
6. concentrationFinally, the filtrate was concentrated
7. custompurified by column chromatography (eluent: dichloromethane-methanol (4:1))

ORD record

ord-fa4336e9719248078117ba88a3c19bea

Source dataset

uspto-grants-1992_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05084459