Pyridine → HCID 15295289, compound

Participants

Reaction Steps

A stirred solution of 4-[5-(4-cyanophenoxy)pentyloxy]-2-hydroxy-benzoic acid (28 g, 82 mmol) in 300 mL of dichloromethane is treated with pyridine (13.3 mL, 164 mmol) and acetic anhydride (9.3 mL, 98.4 retool) and stirred at room temperature for 30 minutes. The reaction is concentrated in vacuo and the residue is partitioned between ethyl acetate and 1N hydrochloric acid. The organic phase is washed with 1N hydrochloric acid and brine, dried over sodium sulfate, and concentrated in vacuo. The resulting 2-acetoxy-4-[5-(4-cyanophenoxy)pentyloxy]-benzoic acid is then dissolved in 300 mL of dichloromethane and treated at 0° C. with oxalyl chloride (8.6 mL, 98.4 mmol) and N,N-dimethylformamide (7.6 mL, 98.4 mmol). This solution is stirred at room temperature for 30 minutes and treated with 30 mL of diisopropylamine at 0° C. After stirring at room temperature for 30 minutes, the reaction is filtered and the filtrate is concentrated in vacuo. The resulting material is partitioned between ethyl acetate and 1N hydrochloric acid. The organic phase is washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford 2-acetoxy-4-[ 5-(4-cyanophenoxy)pentyloxy]-N,N-bis(1-methylethyl)benzamide.

Provenance & Evidence