3-Methoxycinnamonitrile → 3-(3-methoxyphenyl)propan-1-amine

Participants

Reaction Steps

A mixture of trans-3-(3-Methoxyphenyl)-2-propenenitrile (27.6 g, 173 mmol) and PtO2 (2.76 g) in 200 mL of EtOH and 30 mL of CHCl3 was shaken in a Parr apparatus under an atmosphere of 50-60 psi H2 overnight at RT. The reaction mixture was filtered through Celite and concentrated in vacuo to provide a brown solid which was then partitioned between CH2Cl2 and 1N NaOH. The organic phase was separated and the aqueous phase was extracted with CH2Cl2 (3×100 mL). The combined organic layers were then dried over MgSO4, filtered and concentrated in vacuo to provide 24.2 g of the desired product as a yellow oil (85% yield). 1H NMR (CDCl3) δ 7.15-7.22 (m, 1H), 6.70-6.80 (m, 3H), 3.80 (s, 3H), 2.72 (t, J=6.0 Hz, 2H), 2.58-2.65 (m, 2H), 1.70-1.85 (m, 2H).

Provenance & Evidence