P-Anisidine → 2-amino-N-(4-methoxyphenyl)benzamide

Participants

Reaction Steps

A mixture of isatoic anhydride (4.894 g, 30 mmol), 4-methoxyaniline (3.695 g, 30 mmol) and toluene (60 mL) was heated to reflux for 5 h. After cooling, the reaction was filtered. The solid was triturated with CH2Cl2 (500 mL). This supernatant was combined with the above filtrate and concentrate. The residue was dissolved in CH2Cl2, decolorized with activated charcoal and crystallized from CH2Cl2/hexanes to give the title compound as a white solid (5.3 g, 73%); mp 116-7 C; MS(FD): 242.

Provenance & Evidence