2,2'-Dinitrobiphenyl → 2,2'-Biphenyldiamine

Participants

Reaction Steps

Compound 9H was synthesized by an adaptation of a literature procedure, Gillespie et al. (2002) J. Org. Chem. 67:3450-3458. 2,2′-Dinitrobiphenyl (102.0 g, 417.5 mmol) and 10% Pd/C (16.4 g) were combined with 300 mL EtOAc in a hydrogenation vessel. The vessel was pressurized to 40 psi H2 for 3.5 h (when H2 was no longer being consumed). The slurry was filtered through a plug of celite. Rotary evaporation followed by drying on a vacuum line gave pure product as light yellow/orange powder in 100% yield. 1H NMR (CDCl3, 297K, 300 MHz): δ 3.71 (s, 4H), δ 6.79 (dd, 2H, J=8.0, 1.2 Hz), δ 6.84 (td, 2H, J=7.4, 1.2 Hz), δ 7.12 (dd, 2H, J=8.0, 1.5 Hz), δ 7.19 (td, 2H, J=7.4, 1.5 Hz). 13C NMR (CDCl3, 297K, 300 MHz): δ 115.58, δ 118.71, δ 124.62, δ 128.81, δ 131.08, δ 144.22. HRMS (ESI-EMM): m/z=185.1073 ([M+H]+), Δ=2.7 ppm.

Provenance & Evidence