Sodium hydride → 2-(N-t-Butoxycarbonyl-N-methylamino)-4-(4-amino-3,5-dimethylphenoxy)nitrobenzene

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Reaction Steps

4-Amino-3,5-dimethylphenol (1.10 g) was added to a suspension of sodium hydride (0.35 g, 55% (w/w) dispersion in mineral oil) in anhydrous N,N-dimethylformamide and the mixture was stirred at room temperature for 15 minutes. To the mixture was added in small portions 4-chloro-2-(N-t-butoxycarbonyl-N-methylamino)-nitrobenzene and the mixture was stirred at 120° C. for 1 hour. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using hexane: ethyl acetate=3:1 the eluant to afford the title compound (2.27 g, Rf=0.24: thin layer chromatography on a silica gel plate using hexane: ethyl acetate=3:1 as the eluant).

Provenance & Evidence