O-Toluidine → Quinoline

Participants

Reaction Steps

A solution of 3-isobutyryl-4-chloro-8-benzoyloxymethylquinoline (3.68 g, 10 mmol) and 2-methylaniline (2.13 ml, 20 mmol) in dioxan (50 ml) was heated at reflux for 2 hours, then evaporated, taken up in dichloromethane, washed with aqueous sodium bicarbonate, water and brine, dried and evaporated to an oil. This was taken up in 1% methanolic sodium hydroxide solution (100 ml) and stirred vigorously for 1 hour. The methanol was evaporated, water and dichloromethane added, the aqueous phase adjusted to pH 10 and extracted with dichloromethane. The organic extracts were dried, evaporated and chromatographed (silica, gel, 1%-2% methanol in dichloromethane). Trituration of the product fractions with ether followed by recrystallization from aqueous methanol gave 3-isobutyryl-4-(2-methylphenylamino)-8-hydroxymethyl)quinoline (1.46 g, 44%), m.p. 116°-118°.

Provenance & Evidence