Regioselective methylation of 1-benzyl-Δ9, 10-octahydro-4-quinolone

Article abstract of DOI:10.1007/BF00506149

The methylation of 1-benzyl-Δ⁹,¹⁰-octahydro-4-quinolone with methyl iodide in the presence of lithium diethylamide in tetrahydrofuran is a regioselective electrophilic substitution reaction, and, depending on the reaction conditions, takes place in the 3 or 8 position of the quinolone system. Deuteration under the same conditions takes place only in the 3 position.