Sodium Hydroxide → 4-[5-[4-[amino(hydroxyimino)methyl]-3-fluoro-phenoxy]pentyloxy]-N,N-bis (1-methylethyl)benzamide

Participants

Reaction Steps

A stirred solution of 4-[5-(4-cyano-3-fluoro-phenoxy)pentyloxy]-N,N-bis(1-methylethyl)benzamide (360 mg, 0.84 mmol) in 1.7 mL of 1N sodium hydroxide (1.7 mmol) and 10 mL of ethanol is treated with hydroxylamine hydrochloride (120 mg, 1.7 mmol). After refluxing overnight, the reaction is concentrated in vacuo. The resulting material is purified by chromatography on silica gel (500 g) with 60-70% ethyl acetate/hexane as the eluent to afford 4-[5-[4-[amino(hydroxyimino)methyl]-3-fluoro-phenoxy]pentyloxy]-N,N-bis (1-methylethyl)benzamide as a colorless foam;

Provenance & Evidence