HCID 20738641, compound → (4-Amino-3-methoxy-2-methylphenyl)acetonitrile

HRID 2217377Notes

Reaction equation

HRID 2217377 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:15])=[C:5]([CH2:12][C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>C(O)C.[Pd]>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([CH2:12][C:13]#[N:14])=[C:4]([CH3:15])[C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 20738641HCID 20738641, compound

Product 1

HCID 20738650(4-Amino-3-methoxy-2-methylphenyl)acetonitrileYield 103.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (3-methoxy-2-methyl-4-nitro-phenyl)-acetonitrile (1.03 g, 5.0 mmole) in ethanol (100 mL) was added a small amount of 10% palladium on charcoal catalyst and the mixture hydrogenated on the Parr hydrogenator at 45 psi for 3.5 hours. The reaction mixture was filtered through celite and evaporated under reduced pressure to give the (4-amino-3-methoxy-2-methyl-phenyl)acetonitrile as a solid (0.912 g, 100%). 1H NMR (CDCl3) δ: 2.25 (s, 3H), 3.56 (s, 2H), 3.72 (s, 3H), 3.85 (br, 2H), 6.60 (d, 1H, J=8.1 Hz), 6.90 (d, 1H, J=8.1 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-090c9c94706f4e1a990bf3ccf244d96b
Source dataset
uspto-grants-2008_08
Patent number
US07407980B2

Reaction notes

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