HCID 59353071, compound → HCID 59353052, compound

Participants

Reaction Steps

A solution of 1-(cyclopentylidenemethyl)-4-methoxy-2-nitrobenzene (1.8 g; 0.09 M, 7.72 mmol; 1 eq) in MeOH (80 mL) is pumped through the H-Cube™ flow hydrogenator fitted with a 10 mol % Pd/C catalyst cartridge (30×4 mm) heated to 25° C. at 1 bar with the full hydrogen option enabled. The flow rate is set at 1 mL/min. The catalyst is pre-saturated with hydrogen gas for 2 min before passing the substrate through. The solvent is evaporated under reduced pressure and the residue is taken up in HCl 1N and EtOAc. The organic phase is washed with brine then dried over MgSO4, and the solvent is evaporated under reduced pressure to afford 1.02 g (64%) of the title compound as a brown oil. 1H NMR (CDCl3) δ 6.94 (d, J=8.3 Hz, 1H), 6.45-6.35 (m, 2H), 4.45-3.90 (m, 2H), 3.75 (s, 3H), 2.45 (d, J=7.0 Hz, 2H), 2.12 (q, J=7.0 Hz, 1H), 1.78-1.45 (m, 6H), 1.35-1.05 (m, 2H). HPLC (max plot) 89%; Rt 2.86 min. LC/MS: (ES+): 206.1.

Provenance & Evidence