N-{4-[(cyclohexylmethyl)amino]-3-nitrophenyl}acetamide → N-{3-amino-4-[(cyclohexylmethyl)amino]phenyl}acetamide

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Reaction Steps

The above crude product N-{4-[(cyclohexylmethyl)amino]-3-nitrophenyl}acetamide (6.60 g) was hydrogenated in ethyl acetate (300 mL) catalyzed by 10% Pd/C (0.5 g) at 20-30 psi H2 in Parr shaker for 4.5 h at room temperature. After filtration through celite and concentration, 5.08 g (97%) of a purple solid was obtained. which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 1.00 (m, 2H), 1.24 (m, 3H), 1.59 (m, 2H), 1.72 (m, 2H), 1.84 (m, 2H), 2.13 (s, 3H), 2.91 (d, J=6.64 Hz, 2H), 3.37 (s broad, 3H), 6.56 (d, J=8.40 Hz, 1H), 6.69 (dd, J=8.30, 2.25 Hz, 1H), 6.98 (s, 1H), 7.12 (d, J=2.34 Hz, 1H). MS (ESI) (M+H)+: 262.31.

Provenance & Evidence