Stannous Chloride → 4-Amino-3-methylbenzonitrile

HRID 1636773Notes

Reaction equation

HRID 1636773 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[C:5]#[N:6].Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCO.CCOC(C)=O>[NH2:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 28014343-Methyl-4-nitrobenzonitrile

Product 1

HCID 70103164-Amino-3-methylbenzonitrileYield 70.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-methyl-4-nitrobenzonitrile (2.0 g, 12.3 mmol) in 100 mL of EtOH is added SnCl2 (13.9 g, 61.7 mmol). The resulting solution is heated at reflux. After 2 hours, the solution is cooled to ambient temperatures. The solution is poured into 150 mL of ice water. The pH of the solution is adjusted to >7 with a solution of saturated NaHCO3. The solution is diluted with EtOAc and the resulting mixture is filtered through Celite. The filtered solution is separated. The organic layer is dried over MgSO4, filtered and concentrated to give the title compound (1.57 g, 8.7 mmol) as an off-white solid.

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureat reflux
  3. temperaturethe solution is cooled to ambient temperatures
  4. filtrationthe resulting mixture is filtered through Celite
  5. customThe filtered solution is separated
  6. dry with materialThe organic layer is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-877ec3684ef245cf81a966df644d245b
Source dataset
uspto-grants-2000_03
Patent number
US06034093

Reaction notes

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