Water → 3-Azido-4-methylbenzoic acid

Participants

Reaction Steps

A mixture of 1.04 g (5.62 mmol) 3-nitro-4-fluoro benzoic acid and 105 mg of Pd/C in 10 mL of TFA was stirred for 12 h under an H2 atmosphere. The mixture was then filtered through celite and the filter cake was washed with 20 mL of TFA. The pale yellow solution was then stirred under N2 at 0° C. for 10 min and 405 mg (5.87 mmol) of NaNO2 was added in small portions over 15 min. After an additional 15 min, 400 mg (6.15 mmol) of NaN3 was then added carefully in portions. Gas evolved slowly, and after 1 h the mixture was poured over 20 mL of water and 50 mL of ice. After the ice had melted, the resulting precipitate was filtered and washed with water and hexanes, then dried under vacuum to provide 964 mg of Compound 7 as a white powder.

Provenance & Evidence