Methylation of 4-Hydroxy-2-quinolone

Article abstract of DOI:10.1002/ardp.19803130904

The reaction of 4-hydroxy-2-quinolone (1a) with methyl iodide/potassium hydroxide in boiling acetone gave a mixture of 1-methyl-4-methoxy-2-quinolone (1d), 1,3-dimethyl-4-methoxy-2-quinolone (1e), and 1,3,3-trimethyl-2,4-dioxo-1,2,3,4-tetrahydroquinoline (2).As by-product 2,4-dimethoxyquinoline (3) was identified.Under the same conditions 4-methoxy-2-quinolone (1c) yielded 1d, 1e, 2 and 3, while 1-methyl-4-hydroxy-2-quinolone (1b) gave 1d, 1e and 2.