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温度

0 °C

A suspension of 7-bromo-4-chloro-3-nitroquinoline (75.00 g, 260.9 mmol) in 350 mL of dichloromethane was cooled to 0° C. under an atmosphere of nitrogen. The suspension was treated with triethylamine (43.25 mL, 326.1 mmol), which dissolved most of the material. A solution of tert-butyl carbazate (37.93 g, 287.0 mmol) in 250 mL of dichloromethane was added to the reaction mixture over 20 min. The reaction was allowed to slowly come to ambient temperature. After 15 h, the reaction mixture was washed with 5% Na2CO3 solution (2×100 mL) and water (100 mL). The combined aqueous washes were back-extracted with CHCl3 (50 mL). The combined organic portions were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield 99.98 g of tert-butyl N′-(7-bromo-3-nitroquinolin-4-yl)hydrazinecarboxylate as a dark red solid.

1. dissolutiondissolved most of the material
2. customto slowly come to ambient temperature
3. washthe reaction mixture was washed with 5% Na2CO3 solution (2×100 mL) and water (100 mL)
4. extractionThe combined aqueous washes were back-extracted with CHCl3 (50 mL)
5. washThe combined organic portions were washed with brine (100 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure