Hydrochloric Acid → 2-chloro-N1-(2-methyl-1-(naphthalen-2-yl)propan-2-yl)benzene-1,4-diamine

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Reaction Steps

To a mixture of water (50 mL) and iron powder (3.78 g, 67.7 mmol) at 65° C. was added concentrated hydrochloric acid (1.0 mL) dropwise and the mixture was stirred for 15 min. The aqueous layer of the mixture was poured out and a solution of 2-chloro-N-(2-methyl-1-(naphthalen-2-yl)propan-2-yl)-4-nitroaniline (2.4 g, 6.76 mmol) in THF (50 mL) was added to the above processed iron powder. The mixture was stirred further at 65° C. for 30 min. The mixture was then cooled to rt and filtered, and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=8:1) to give the title compound as a white solid (1.86 g, 84%).

Provenance & Evidence