Ammonia → N-(4-Nitrophenyl)-4-(4-pyridinylamino)benzamide

Participants

Reaction Steps

Compound D2 (172 mg, 0.80 mmol) was refluxed in SOCl2 (5 mL) containing a catalytic amount of DMF for 1 h (until a clear solution was obtained). The reaction mixture was cooled to room temperature and excess SOCl2 was removed under vacuum. Dioxane (10 mL) was added to the residue, and then removed under vacuum. The residue was cooled in a dry ice-acetone bath, p-nitroaniline (112 mg, 0.81 mmol) and pyridine (1.3 mL) were added, followed by Et3N (0.3 mL), and the mixture was stirred at room temperature for 20 min, and then refluxed for 1 h. The reaction mixture was cooled to room temperature and diluted with H2O, and then basified with aqueous NH3 and stirred for 30 min. The resulting precipitate was filtered, and washed sequentially with water, hexane and CH2Cl2. The crude product was dissolved in MeOH and then adsorbed onto silica gel, and the resulting adsorbate chromatographed on silica gel, eluting with 0-10% MeOH:CH2Cl2, to give D3 (85 mg, 32%); mp 298-302° C. (MeOH); 1H NMR [(CD3)2SO] δ 10.64 (s, 1 H, NH), 9.21 (s, 1 H, NH), 8.30-8.24 (m, 4 H, ArH), 8.09-8.05 (m, 2 H, ArH), 8.00-7.98 (m, 2 H, ArH), 7.34-7.31 (m, 2 H, ArH), 7.07-7.05 (d, m, 2 H, ArH);LCMS 235+ve.

Provenance & Evidence