3-Nitrophenylacetonitrile → (3-Amino-phenyl)-acetonitrile

HRID 1351407Notes

Reaction equation

HRID 1351407 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.O.O.[Sn](Cl)Cl>C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 121253-NitrophenylacetonitrileHCID 61436Stannous chloride dihydrate

Product 1

HCID 4847850(3-Amino-phenyl)-acetonitrile

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

3-Nitrophenylacetonitrile (6.87 g, 42 mmol) and tin(II)chloride dihydrate (50 g, 220 mmol) in ethyl acetate (125 ml) were stirred at room temperature for 72 hours. The reaction was diluted with ethyl acetate and saturated aqueous sodium bicarbonate solution was added. The resulting precipitate was filtered off and the filtrate extracted with ethyl acetate (3×). The combined organic solutions were dried (MgSO4), filtered and evaporated under reduced pressure to afford the title compound as a pale yellow oil, 5.33 g.

Workup

  1. additionwas added
  2. filtrationThe resulting precipitate was filtered off
  3. extractionthe filtrate extracted with ethyl acetate (3×)
  4. dry with materialThe combined organic solutions were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ded7ad112cc84513bd58d8176f3a1d52
Source dataset
uspto-grants-2007_05
Patent number
US07217714B1

Reaction notes

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