Hydrochloric Acid → 4-Propylpyridin-2-amine

Temperature

140 °C

To a solution of 4-propylpyridine (10.0 g, 82.5 mmol) in toluene (170 mL), sodium amide (6.4 g, 165 mmol) was added at room temperature, and the mixture was stirred at 140° C. for 2 days. Under ice-cold conditions, the reaction solution was added 6N aqueous solution of hydrochloric acid (30 mL), and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate/1% triethylamine), and the title compound (5.70 g (yield 51%)) was obtained as a red-brown solid.

1. extractionextracted with ethyl acetate
2. washThe organic layer was washed with brine
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated in vacuo
5. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate/1% triethylamine)

ORD record

ord-a03d1944fe274bf393149e71d3fdb1fd

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08551985B2