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

Participants

Reaction Steps

A stirred solution of 4-[5-(4-cyanophenoxy)-pentyloxy]-N,N-bis(1-methylethyl)benzamide (300 mg, 0.73 mmol) in 2 mL of water and 8 mL of ethanol is treated with sodium hydroxide (32 mg, 0.81 mmol) and hydroxylamine hydrochloride (56 mg, 0.81 mmol). After refluxing overnight, the reaction is partitioned between dichloromethane and brine. The organic phase is dried over sodium sulfate, and concentrated in vacuo. The resulting material is purified by chromatography on silica gel (10 g) with 70-80% ethyl acetate/hexane as the eluent to afford 4-[5-[4-[amino(hydroxyimino)methyl]phenoxy]pentyloxy]-N,N-bis -(1-methylethyl)benzamide as colorless crystals, m.p.=146°-149° C.;

Provenance & Evidence