In response to the current problems of organic chemistry basic experiments are outdated and lack of systematization, we strengthen the exploration of experimental teaching "gender once". In this paper, an innovative comprehensive organic chemistry experiment for the dimethylation of 6-amino-1, 2, 3, 4-tetrahydro-1-naphthoneone was designed. The substitution reaction was carried out under alkaline conditions with iodomethane as the methylation reagent to generate dimethyl substitution products, and the products were structurally characterized by nuclear magnetic resonance hydrogen spectroscopy (1H NMR), nuclear magnetic resonance carbon spectroscopy (13C NMR), and high performance liquid chromatography. This experiment contains learning contents such as literature search, experimental design, experimental operation, sample characterization and data analysis, and students can improve both theoretical knowledge and practical operation to enhance their overall quality.