6-Chloro-2-tetralone (I) was converted to its pyrrolidine enamine (II) in refluxing toluene. Condensation with acrylamide afforded 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinolin-3-one (III). Methylation with iodomethane and potassium tert-butoxide and tert-butanol afforded the N-methyl derivative (IV), which was reduced with triethylsilane in the presence of trifluoroacetic acid. The crude trans-8-chloro-4-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (V) was purified by recrystallization from ethyl acetate.