Hydrochloric Acid → Tert-butyl 2-(4-nitrophenyl)ethyl hydrazine-1,2-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-nitrophenyl)ethanol (5.015 g, 30.00 mmol) in anhydrous tetrahydrofuran (50 ml) was added 1,1′-carbonyldiimidazole (5.839 g, 36.01 mmol), and the mixture was stirred at room temperature for 30 min. tert-Butyl carbazate (5.956 g, 45.06 mmol) was added, and the mixture was stirred at room temperature for 16 hr and further at 50° C. for 8 hr. 0.5M Hydrochloric acid (100 ml) and ethyl acetate (100 ml) were added to the reaction mixture, and the mixture was stirred, stood still and then partitioned. The organic layer was washed with 0.5M hydrochloric acid, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 200 g, ethyl acetate:hexane=4:6→5:5) to give tert-butyl 2-(4-nitrophenyl)ethyl hydrazine-1,2-dicarboxylate (9.780 g, quantitative) as a slightly yellow solid.

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