Doebner-Miller reaction the 4- nitrocinnamaldehyde and 2-methylaniline in concentrated HC1 give the corresponding 8-methyl-2-phenylquinoline (3: R = 4'-N02) directly. The asymmetric Friedel-Crafts-type alkylation in aqueous media reaction of 4-Nitrocinnamaldehydr with N-methyl indole using trifluoroacetic acid (TFA) salt of the PEG-PS-supported prolyl peptide having the polyleucine tether as a catalyst. 4-Nitrocinnamaldehyde has been used in the preparation of 2, 2?-[(E)-3-(4-nitrophenyl) prop-2-ene-1,1-diyl] bis(3-hydroxy-5, 5-dimethylcyclohex-2-en-1-one).