Ammonium Hydroxide → 2-(Pyridin-3-yloxy)ethanamine

Temperature

125 °C

The 2-chloro-1-(3-pyridyloxy)ethane (1.23 g, 7.80 mmol) was dissolved in methanol (25 mL) and added to concentrated ammonium hydroxide solution (29.7%, 14.8 M, 55 mL) in a heavy-walled glass pressure-tube apparatus. The tube was sealed and the mixture was stirred and heated at 125° C. (oil bath temperature) for 42 h. After cooling, the mixture was concentrated by rotary evaporation. Saturated NaCl solution (10 mL) was added to the residue, and the solution (pH 6) was extracted with ether (3×25 mL) to remove impurities. The aqueous layer was diluted with saturated NaCl solution (15 mL) and basified to pH 12 with 10% NaOH solution (5 mL). The mixture was extracted with chloroform (4×50 mL). The combined light-yellow chloroform extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation to a residue that was dried briefly under high vacuum to give 0.390 g (36.2%) of a light-yellow oil.

1. customThe tube was sealed
2. temperatureAfter cooling
3. concentrationthe mixture was concentrated by rotary evaporation
4. additionSaturated NaCl solution (10 mL) was added to the residue
5. extractionthe solution (pH 6) was extracted with ether (3×25 mL)
6. customto remove impurities
7. additionThe aqueous layer was diluted with saturated NaCl solution (15 mL)
8. extractionThe mixture was extracted with chloroform (4×50 mL)
9. dry with materialThe combined light-yellow chloroform extracts were dried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated by rotary evaporation to a residue that
12. customwas dried briefly under high vacuum

ORD record

ord-eb3d74b1be01492cb0f8ecaa5adab776

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627648B1