Citric Acid → HCID 54225044, compound

Participants

Reaction Steps

3-Amino-N-[2-(4-hydroxyphenyl)ethyl]phthalimide (110 mg, 0.390 mol, 1 eq) was dissolved in acetone (30 ml), and to this solution were added 1-chloro-1-pentanone (70.5 mg, 0.585 mmol, 1.5 eq) and triethylamine (0.081 ml, 0.585 mol, 1.5 eq) in this order. The mire was refluxed under heating for 30 minutes. This reaction mixture was cooled to room temperature. Ice water (10 ml) and citric acid (10 ml) were added, and the mixture was extracted twice with ethyl acetate (20 ml). The organic layers were combined, washed with saturated brine (30 ml) and dried over anhydrous sodium sulfate. After the drying agent was filtered off, the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=5/1) to give 4-[2-(1,3-dioxo4-pentanoylamino-1,3-dihydroisoindol-2-yl)ethyl]phenyl pentanoate (80.2 mg, 56.2%) as colorless crystals.

Provenance & Evidence