(2-Methoxyphenoxy)acetonitrile → 2-(2-Methoxyphenoxy)ethyl amine
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[O:5][CH2:6][C:7]#[N:8].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[O:5][CH2:6][CH2:7][NH2:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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+).