(2-Methyl-3-nitrophenyl)acetonitrile → 3-Amino-2-methylphenylacetonitrile

HRID 1106740Notes

Reaction equation

HRID 1106740 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:11][C:12]#[N:13].[H][H]>C(OCC)(=O)C.[Pd]>[NH2:8][C:7]1[C:2]([CH3:1])=[C:3]([CH2:11][C:12]#[N:13])[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 13530896(2-Methyl-3-nitrophenyl)acetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 221703203-Amino-2-methylphenylacetonitrileYield 80.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(2-Methyl-3-nitro-phenyl)-acetonitrile (16.6 g ) was dissolved in 400 ml of ethyl acetate and 0.83 g of 10% palladium on carbon (Degussa type) was added; and the reaction mixture was placed under 50 lb/in2 of hydrogen on the Parr shaker for 4 hr. The catalyst was filtered off; the solvent was evaporated; and the residue was purified by flash chromatography on silica gel eluting with ethyl acetate:hexane (2:3), yielding 11.1 g of (3-amino-2-methyl-phenyl)-acetonitrile as a white solid. ##STR119##

Workup

  1. customfor 4 hr
  2. filtrationThe catalyst was filtered off
  3. customthe solvent was evaporated
  4. customand the residue was purified by flash chromatography on silica gel eluting with ethyl acetate:hexane (2:3)

Sources & evidence

ORD record
ord-59276a29b2b049b59c58947aef75a872
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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