Stannous Chloride → 3,4-Diamino-5-nitrobenzonitrile

HRID 1586090Notes

Reaction equation

HRID 1586090 reaction equation
[NH2:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:13]([O-])=O.Cl[Sn]Cl>CCO>[NH2:13][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]=1[NH2:1])[C:6]#[N:7]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 212178444-Amino-3,5-dinitrobenzonitrile

Product 1

HCID 212178463,4-Diamino-5-nitrobenzonitrileYield 42.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4-amino-3,5-dinitrobenzonitrile (9.4 g, 0.045 mol) in EtOH (100 mL) was added SnCl2 (30 g, 0.16 mol). The mixture was refluxed for 1 h. The reaction was then filtered and the filtrate concentrated to afford 3,4-diamino-5-nitrobenzonitrile (3.4 g, 42%) of an orange solid.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. filtrationThe reaction was then filtered
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-af5fc443f350485a82517404f2651223
Source dataset
uspto-grants-1999_08
Patent number
US05942532

Reaction notes

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