Dichloromethane → [1,1'-Biphenyl]-3-amine, 5-methyl-

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Reaction Steps

Pd/C (10 wt %, 161 mg, 0.151 mmol) was added to a solution of 3-methyl-5-nitrobiphenyl (322 mg, 1.51 mmol) in ethyl acetate (10 mL) and acetic acid (1 mL). The reaction mixture was stirred under an atmosphere of H2 (balloon) for 3 hours and then dichloromethane (5 mL) was added. The reaction mixture was filtered through CELITE, washed with ethyl acetate and concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes) provided 5-methylbiphenyl-3-amine as a brown oil. 1H NMR (400 MHz, CDCl3) δ 7.58 (d, J=7.6 Hz, 2H), 7.43 (t, J=7.6 Hz, 2H), 7.34 (t, J=7.3 Hz, 1H), 6.85 (s, 1H), 6.75 (s, 1H), 6.55 (s, 1H), 2.35 (s, 3H).

Provenance & Evidence