Methanol → 3-(Phenylethynyl)aniline

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To a 5-liter multi-necked flask fitted with a mechanical stirrer, reflux condenser, and thermometer was charged 215.6 g (0.96 mol) of 3-phenylethynylnitrobenzene obtained as described above, 600.2 g (2.5 mol) of sodium sulfide nonahydrate, 2 liters of methanol, and 500 ml of distilled water. The system is brought to 70° C. for 3 hours at which point the reduction is complete by thin layer chromatography. The reaction mixture is cooled to room temperature and the methanol removed by a rotary evaporator. The concentrate is added to a separatory funnel along with 1 liter of toluene. The toluene layer is separated and washed with distilled water until neutral to pH paper. Concentration of the toluene solution followed by vacuum distillation gave 131 g (0.68 mol, 71% yield) of 3-phenylethynylaniline.

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