Sulfuric Acid → Cyclohexanone

Participants

Reaction Steps

Compound 11 was reduced with Na(Hg) to 1-amino-4-methylacridine 13 Heating compound 13 with acetylacetone and catalytic amounts of acid gave pure adduct 14, upon chromatography. Specifically, compound 14 was obtained by warming of compound 13 with acetylacetone in amylalcohol with traces of H2SO4 at 130° C. for 1.5 hr. The structure of compound 14 C19H16N2O (eims, m/z 288, 100%) 1-acetyl-2,6-dimethylpyrido[2,3,4-k,l]acridine was elucidated mainly from its NMR data, by comparison of the chemical shifts with those of other pyridoacridines as described by He Hay-Yin et al., J.O.C., 56, 5369 (1991). Reacting compound 13 with cyclohexanone, instead of acetylacetone, gave compound 15. Specifically, compound 15 was obtained from cyclohexanone and compound 13 under the same conditions as compound 14.

Provenance & Evidence