3-Methoxy-4-nitrobenzonitrile → 4-Amino-3-methoxybenzonitrile

HRID 1511838Notes

Reaction equation

HRID 1511838 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-])=O)[C:6]#[N:7]>C(OCC)(=O)C.[Pd]>[NH2:11][C:10]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 108992273-Methoxy-4-nitrobenzonitrile

Product 1

HCID 118159314-Amino-3-methoxybenzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To the suspension of 3-methoxy-4-nitrobenzonitrile (11.4 g, 64 mmol) in ethyl acetate (60 mL) was added 10% Pd/C (1 g). The reaction mixture was vigorously shaken in a Parr under an atmosphere of hydrogen (50 psi) at room temperature for 45 min. The mixture was filtered through a short pad of celite, and the filtrate was concentrated to give 4-amino-3-methoxy-benzonitrile as a yellow oil, which solidified at stand (9.5 g, 95%)

Workup

  1. filtrationThe mixture was filtered through a short pad of celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6fb059879def42c883139bdf0a00fa3c
Source dataset
uspto-grants-2012_07
Patent number
US08217044B2

Reaction notes

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