Ammonia → 3-Amino-5-methoxy-[1,1'-biphenyl]-4-carbonitrile

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Reaction Steps

A solution of 3-fluoro-5-methoxy-[1,1′-biphenyl]-4-carbonitrile (3, 4.0 g, 17.6 mmol) in ammonia saturated DMSO (100 mL) was heated in an autoclave at 150° C. for 18 h. After this time, the mixture was cooled to room temperature, concentrated and purified by silica gel chromatography eluting with ethyl acetate in hexane (0-100%) to afford the title compound (2.06 g, 52%) as a light yellow solid: 1H NMR (500 MHz, CDCl3) δ7.54-7.52 (m, 2H), 7.46-7.43 (m, 2H), 7.41-7.38 (m, 1H), 6.52 (d, J=1.0 Hz, 1H), 6.43 (d, J=1.0 Hz, 1H), 4.43 (br s, 2H), 3.93 (s, 3H).

Provenance & Evidence