Nitric Acid → HCID 58368547, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 5-chloro-2-hydroxy-4-[(trimethylsilyl)ethynyl]benzoate (15 g, 53 mmol) in acetic acid (110 mL) at 55° C. was treated with a solution of nitric acid (7.8 mL, 190 mmol) in acetic acid (7.8 mL, 140 mmol) dropwise and stirred at 55° C. for 30 minutes. The reaction mixture contained only starting material and was treated with an additional solution of nitric acid (2.2 mL, 53 mmol) in acetic acid (2.2 mL, 39 mmol) dropwise and stirred at 55° C. for 1.5 hour. The reaction mixture was cooled to 0° C. and treated with ice followed by cold water. The reaction mixture was stirred until the ice melted, filtered, washed with cold water, and air dried to give the desired product (11.7 g, 67%) as a tan solid. This material was used without further purification. LCMS for C13H15ClNO5Si (M+H)+: m/z=328.0; Found: 327.8.

Provenance & Evidence