Carbonate Ion → 4,4,8-Trimethyl-3,4-dihydroquinolin-2(1H)-one

Participants

Reaction Steps

N-(1-oxo-3-methyl-but-2-en-yl)-2-methylaniline (0.5 g) was added with stirring to 98% w/w sulphuric acid (10 cm3) at 0°. After 2 hours at room temperature (20°) the mixture was poured carefully onto ice (30 g) and the resulting solution was basified to pH 9 with saturated carbonate solution. The mixture was then extracted wilth dichloromethane (2×200 cm3), and the combined and dried (MgSO4) organic extracts were evaporated in vacuo to give a solid which was chromatographed on silica (Merck "MK 60.9385" [Trade mark]). Elution with dichloromethane, followed by combination and evaporation of appropriate fractions gave the title compound, m.p. 120° (0.21 g).

Provenance & Evidence