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

HRID 354061Notes

Reaction equation

HRID 354061 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)-acetonitnle (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-814d6b459bba438bb1b03eccae94305e
Source dataset
uspto-grants-2004_06
Patent number
US06756395B2

Reaction notes

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