Ammonia → Ethyl acetate hexane

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While stirring a mixture comprising 59 mg of 4-hydroxy-6-fluorophenanthridine, 85 mg of 2-amino-5-diethylaminotoluene hydrochloride (21) and 4 ml of ethanol at 20° C., a solution comprising 258 mg of silver nitrate dissolved in 0.8 ml of water was added thereto drop-by-drop. Next, with 0.84 ml of 25% ammonia solution added, reaction was allowed to proceed at 20° C. for a period of 24 hr. After the completion of the reaction, the reacted solution was introduced into water. After extraction by chloroform, the extract was concentrated. After purification by column chromatography, 29 mg of indoaniline described in the exemplified compound 3-131 was obtained as deep blue crystal on recrystallization from hexane-ethyl acetate solvent (yield 27.1%).

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