Hydrazine → N-Phenanthridin-6-yl-N'-o-tolylhydrazine hydrochloride

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Reaction Steps

A solution of o-tolylhydrazine hydrochloride (7.6 g, 47 mmol) in dichloromethane (450 ml) is extracted by shaking three times each with saturated aqueous sodium hydrogencarbonate solution (90 ml each time) and demineralized water. The organic phase is dried over sodium sulfate, filtered and concentrated to dryness. Yield: 4.9 g (86%). The hydrazine (4.8 g, 39 mmol) is dissolved in ethanol (100 ml) and admixed under argon with 6-chlorophenanthridine (A. G. Mikhailovskii, V. S. Shklyaev, Chem. Heterocycl. Comp. 1992, 445) (7.0 g, 33 mmol). The mixture is stirred under reflux for 16 h. After cooling to room temperature, the resulting precipitate is filtered off and washed with ethanol and petroleum ether. Yield: 9.3 g (85%).

Provenance & Evidence