Triethylamine → tert-butyl N'-(3-nitroquinolin-4-yl)hydrazinecarboxylate

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Reaction Steps

A solution of 4-chloro-3-nitroquinoline (5.00 g, 24.0 mmol) in 120 mL of anhydrous CH2Cl2 was treated with triethylamine (6.7 mL, 48.2 mmol) and tert-butyl carbazate (3.20 g, 24.2 mmol). After stirring under nitrogen for 2.5 hour (h), an additional portion of tert-butyl carbazate (3.2 g, 24.2 mmol) was added. After stirring overnight, the deep red solution was washed with H2O (2×) and brine. The organic portion was dried over Na2SO4 and concentrated to give a red foam. The material was passed through a SiO2 column eluting with 2.5% methanol/CH2Cl2. The resulting red powder was treated with 5:1 hexanes/CH2Cl2 and filtered. The solid was washed several times with hexanes and was dried under vacuum to give tert-butyl N′-(3-nitroquinolin-4-yl)hydrazinecarboxylate (4.97 g) as an orange powder.

Provenance & Evidence