(2-Methoxyphenoxy)acetonitrile → 2-(2-Methoxyphenoxy)ethyl amine

Temperature

0 °C

To a solution of 2-(2-methoxy-phenoxy)acetonitrile (5 g, 31 mmol) in anhydrous ethyl ether (100 ml) was added lithium aluminum hydride (1.6 g, 40 mmol) portionwise. The reaction mixture was heated to reflux for 3 hours and then cooled to 0° C. The reaction was quenched with 1N hydrochloric acid and diluted with water (PH=1, aqueous layer). The mixture was extracted with ethyl acetate (3×150 ml), neutralized with 50% sodium hydroxide to pH>10, and extracted again with more ethyl acetate (3×100 ml). The combined organic layers were washed with brine (3×150 ml), dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum to afford 2.85 g (56%) of product as an oil; MS EI m/e 167 (M+).

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 3 hours
3. customThe reaction was quenched with 1N hydrochloric acid
4. additiondiluted with water (PH=1, aqueous layer)
5. extractionThe mixture was extracted with ethyl acetate (3×150 ml)
6. extractionextracted again with more ethyl acetate (3×100 ml)
7. washThe combined organic layers were washed with brine (3×150 ml)
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationfiltered
10. customThe solvent was removed under vacuum

ORD record

ord-e86c5fbf70354b4b934888b6fdad63e8

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06110956