Hydrochloric Acid → 1-Methyl-7-nitroisatoic anhydride

Participants

Reaction Steps

To a suspension of 0.1656 g (4.14 mmoles) of sodium hydride (60% in mineral oil) in 20 mL DMF was added a solution of 0.6584 g (3.16 mmoles) of 4-nitroisatoic anhydride in 20 mL DMF. After stirring a few minutes at room temperature, a clear orange solution formed. 0.2615 g (3.2 mmoles) of methyl iodide was added to the reaction, and the mixture was stirred at room temperature for 4 hours. The reaction was poured into 50 mL of cold 1 N HCl, and the resulting bright orange precipitate was filtered and washed sequentially with water and ether to give 608.3 mg (86%) of product. 1H NMR (CO(CD3)2, 400 MHz,) δ 3.69 (s, 3H, —NCH3—), 8.12 (dd, J=8.8 Hz, 2 Hz, 1H, ArH), 8.2 (d, J=2 Hz, 1H, ArH), 8.34 (d, J=8.4 Hz, 1H, ArH).

Provenance & Evidence