4-Aminobenzamide → 4-amino-N-(3,5-dimethylphenyl)benzamide

Participants

Reaction Steps

Using general procedure A, 4-aminobenzamide (170 mg, 1.25 mmol) was coupled with 5-iodo-m-xylene (150 μL, 1.04 mmol). The crude product was purified by flash chromatography on silica gel (2×20 cm; hexane-ethyl acetate 2:3; 15 mL fractions). Fractions 9-18 provided 246 mg (98% yield) of the product as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.74-7.69 (m, 2H), 7.66 (br s, 1H), 7.28 (s, 2H), 6.78 (s, 1H), 6.74-6.69 (m, 2H), 4.05 (br s, 2H), 2.33 (s, 6H). 13C NMR (100 MHz, CDCl3): δ 165.7, 150.3, 139.1, 138.6, 129.2, 126.2, 124.8, 118.2, 114.6, 21.8.

Provenance & Evidence