Stannous Chloride → 4-Amino-2,3-dimethylbenzonitrile

HRID 1269862Notes

Reaction equation

HRID 1269862 reaction equation
[Sn](Cl)Cl.[CH3:4][C:5]1[C:12]([CH3:13])=[C:11]([N+:14]([O-])=O)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]>C(O)C>[NH2:14][C:11]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([CH3:4])[C:12]=1[CH3:13]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 229337662,3-Dimethyl-4-nitrobenzonitrile

Product 1

HCID 199903354-Amino-2,3-dimethylbenzonitrileYield 93.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin dichloride (12.24 g, 54.2 mmol) was added to a solution of 2,3-dimethyl-4-nitrobenzonitrile (2.73 g, 15.5 mmol) in ethanol (94 ml) at room temperature, and the reaction was carried out for 5 hours under reflux conditions. After cooling, the reaction mixture was concentrated, and the resulting residue was diluted with ethyl acetate and then washed with a saturated aqueous sodium hydrogencarbonate solution. After the insoluble material was filtered off, the filtrate was separated and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate and distilled to remove the solvent, whereby 4-amino-2,3-dimethylbenzonitrile (2.12 g, 93.6%) was obtained.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated
  3. additionthe resulting residue was diluted with ethyl acetate
  4. washwashed with a saturated aqueous sodium hydrogencarbonate solution
  5. filtrationAfter the insoluble material was filtered off
  6. customthe filtrate was separated
  7. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. distillationdistilled
  10. customto remove the solvent

Sources & evidence

ORD record
ord-13f2018725274b2fac8d9b995efa6351
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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