3-Bromoaniline → HCID 86083506, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 4-chloro-4-(3,4-dinitrophenyl)butanone (366.3 mg, 1.2 mmol.), 3-bromoaniline (220 mg, 1.3 mmol.) and N,N-dimethylacetamide (0.3 mL) were combined and heated to 120° C. over 17 hours under a nitrogen atmosphere. The mixture was then cooled to room temperature and partitioned with ethyl acetate and water. The organic layer was washed twice with additional water, then brine and dried over anhydrous sodium sulfate. Filtration and concentration followed by purification of the residue by silica gel flash chromatography (100% ethyl acetate eluent) gave 1-(3-bromophenyl)-5-(3,4-dinitrophenyl)pyrrolidin-2-one (132 mg, 28% yield) as an amorphous residue. The material thus obtained is contaminated by variable amounts of 5-(3,4-dinitrophenyl)dihydrofuran-2(3H)-one as a side product and is carried forward without further purification. MS (EI) for C16H12N3O5Br: 407 (MH+).

Provenance & Evidence