[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([CH3:12])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1.CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([CH3:12])[CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1
To a solution of 2-(3-methoxyphenyl)propanenitrile (1.33 g, 8.26 mmol) in THF (10 mL) at room temperature was added lithium aluminum hydride (9.1 mL, 1M in THF, 9.1 mmol). The reaction was stirred overnight. More lithium aluminum hydride (0.5 mL) was added and the reaction was refluxed for 4 h. 1 N HCl was added carefully to quench the reaction. It was diluted with ether, washed with H2O. Aqueous layer was treated with NaOH and extracted with CH2Cl2. CH2Cl2 layer was washed with saturated NaCl, dried and concentrated to give 2-(3-methoxyphenyl)-propan-1-amine (761 g, 56% yield) as a pale yellow oil. HPLC retention time (Method C)=1.59 min. LC/MS (ESI) (M+H)+=166.07. 1H NMR (CDCl3, 400 MHz) δ ppm 1.24 (d, J=6.85 Hz, 3H), 2.65-2.77 (m, 1H), 2.85 (d, J=8 Hz, 2H), 3.80 (s, 3H), 6.71-6.84 (m, 3H), 7.20-7.26 (m, 1H).
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