4-Chloro-2-methylbenzaldehyde → 3-Chloro-5-[2-(4-chloro-2-methyl-phenyl)-4-hydroxy-3-isobutyryl-5-oxo-2,5-dihydro-pyrrol-1-yl]-benzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-amino-5-chloro-benzonitrile (2.4 g, 15.7 mmol), 4-chloro-2-methyl-benzaldehyde (2.4 g, 15.7 mmol) and 5-methyl-2,4-dioxo-hexanoic acid ethyl ester (2.9 g, 15.7 mmol) in acetic acid (15 mL) was stirred at 120° C. for 16 h. The reaction mixture was allowed to cool to rt, concentrated, diluted with acetonitrile (15 mL), and stirred for 4 h at rt. The resulting precipitate was collected by vacuum filtration and dried to afford 1.8 g of the title compound. tR: 6.50 min (HPLC 2); ESI-MS: 429 [M+H]+ (LC-MS 2); Rf=0.27 (hexane/EtOAc, 1:1).

Provenance & Evidence