HCID 14256049, compound → 4-[2-(3,4,5-trimethoxyphenyl)ethyl]aniline

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Reaction Steps

A solution of nitrostilbene 6l (250 mg, 0.8 mmol) in EtOAc (20 mL) was hydrogenated at 30 psi in the presence of 10% Pd-C (25 mg) at room temperature for 4 h, and the catalyst was filtered off. Evaporation of the solvent and crystallization of the residue from hexanes gave the amine 8z (180 mg, 80%); mp 84°-5° C; IR (KBr) 3450, 3400, 3020, 2920, 2840, 1600, 1580, 1520, 1330, 1240, 1120, 980 cm-1 ; 1H NMR (CDCl3, 300 MHz) d 6.98 (d, J=8.2 Hz, 2H), 6.63 (d, J=8.2 Hz, 2H), 6.63 (d, J=8.2 Hz, 2H), 6.37 (s, 2H), 3.83 (s, 9H), 3.57 (bs, 2H), 2.80 (s, 4H); CIMS (isobutane) m/e 288 (MH+, 100). Anal. (C17H21NO3) C, H.

Provenance & Evidence