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

HRID 2382148Notes

Reaction equation

HRID 2382148 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][NH2:9].C(=O)([O-])O.[Na+].NN.[Cl:18][C:19]1[N:20]=[C:21]2[C:26](=[C:27]3[C:32]=1[CH:31]=[CH:30][CH:29]=[CH:28]3)[CH:25]=[CH:24][CH:23]=[CH:22]2>ClCCl.C(O)C.O>[ClH:18].[CH:25]1[C:26]2[C:21](=[N:20][C:19]([NH:9][NH:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:10])=[C:32]3[C:27]=2[CH:28]=[CH:29][CH:30]=[CH:31]3)[CH:22]=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 9321HydrazineHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 2699686-ChlorophenanthridineHCID 516892Sodium Bicarbonate

Product 1

HCID 67128317N-Phenanthridin-6-yl-N'-o-tolylhydrazine hydrochloride

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  1. dry with materialThe organic phase is dried over sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated to dryness
  4. temperatureunder reflux for 16 h
  5. filtrationthe resulting precipitate is filtered off
  6. washwashed with ethanol and petroleum ether

Sources & evidence

ORD record
ord-d1165021100948ffb994295719e91617
Source dataset
uspto-grants-2012_09
Patent number
US08258297B2

Reaction notes

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