2-(Dimethylamino)ethanol → 908117-05-5

Sodium hydride (159 mg, 60% mineral oil dispersion, 3.98 mmol) was placed in a dried flask under a nitrogen atmosphere, followed by sequential addition of anhydrous toluene (10 ml) and 2-dimethylaminoethanol (177 mg, 2.0 mmol) with a syringe. After the resulting mixture was stirred at room temperature for 40 minutes, 4-amino-2-chloropyridine (203 mg, 1.59 mmol) was added, followed by heating to reflux for 16 hours. The reaction mixture was cooled, which was subsequently added dropwise slowly onto ice water, followed by extraction twice with ethyl acetate (10 ml). The organic layer was washed with brine (10 ml), and dried over sodium sulfate, followed by distilling off under reduced pressure, to obtain a crude product as a pale brown solid (180 mg).