O-Phenylenediamine → 2-(2-Aminophenylamino)-N-isopropyl-N-phenyl acetamide

Participants

Reaction Steps

To a stirred solution of 40 g (385 mmol) of phenylenediamine is added 75 g (543 mmol, 1.4 equiv.) of potassium carbonate. The suspension is stirred at RT and a solution of 99 g (386.5 mmol, 1 equiv.) of 2-Bromo-N-isopropyl-N-phenyl acetamide in 15 mL THF is added dropwise. The resulting suspension is stirred at RT for 16 h and diluted with 1 L H2O and 1 L EtOAc. The Organics were washed with H2O (3×500 mL), brine (500 mL), dried (MgSO4), and the solvents removed in vacuo. Purification by silica gel flash column chromatography using hexane/EtOAc 8/2 as eluent afforded 71 g of a yellow solid: mp. 110°-112° C.; 1H NMR (CDCl3, 300 MHz) δ7.48-7.44 (m, 4H), 7.18-7.15 (m, 2H), 6.69-6.59 (m, 3H), 6.21-6.19 (m, 1H), 5.11-4.98 (m, 1H), 3.4 (s, 2H), 1.09 (d, 6H, J=7).

Provenance & Evidence