Alkaloids of the Australian Rutaceae: Lunasia quercifolia. I. 7-Methoxy-1-methyl-2-4-quinolone

Abstract

Bark of Lunasia quercifolia contains c. 4-4.5 per cent. alkaloids consisting of c. 3-3.5 per cent. water-soluble bases and c. 1 per cent. tertiary bases. Three component tertiary bases have been isolated ; these are the previously described alkaloids lunacrine and lunine and an undescribed base C₁₇H₁₅O₂N. This new base is shown by degradative processes and by synthesis to be 7-methoxy-1-methyl-2-phenyl-4-quinolone (I). The products of the action of nitric acid on the alkaloid include mono- and dinitro derivatives which undergo hydrolytic fission, giving rise to 2-methylamino-o-nitroacetophenones.