2-Nitroanisole → HCID 20248128, compound

Participants

Reaction Steps

A mechanically stirred mixture of 66.0 ml (0.51 mol) of freshly distilled 4-methoxy-2-methylaniline, 50.5 ml (0.41 mol) of freshly distilled o-nitroanisole, 189 g (3.37 mol) of finely powdered potassium hydroxide, and 945 ml of toluene was heated to reflux (initially exothermic) for 1 hour. The mixture was then cooled to room temperature, filtered, and the filter cake washed with toluene, 1% methanol/dichloromethane, and dichloromethane. The solvent from the combined filtrate and washings was removed in vacuo to yield 86 g of black solid. The black material was then flash filtered through silica gel eluting with ether and the fractions containing the desired phenazine (Rf =0.22 on silica gel, dichloromethane) were combined, concentrated in vacuo and purified by flash chromatography, eluting with dichloromethane. A final chromatography on a Waters Prep-500 chromatograph (6:1 hexane-acetone) followed by recrystallization from a hexane/toluene mixture afforded 12.3 g of the title compound as yellow needles, melting point 201°-202° C.

Provenance & Evidence