2-Methoxy-4-nitrobenzonitrile → 4-Amino-2-methoxybenzonitrile

HRID 2272615Notes

Reaction equation

HRID 2272615 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6]>[Pd].CO>[NH2:11][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([O:2][CH3:1])[CH:10]=1

Participants

4

Reactant 1

HCID 2918672-Methoxy-4-nitrobenzonitrile

Product 1

HCID 2327354-Amino-2-methoxybenzonitrileYield 108.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-methoxy-4-nitrobenzonitrile (750 mg, 4.21 mmol) and palladium on carbon (50 mg, 0.47 mmol) in methanol (15 mL) was stirred at room temperature for 48 hr under hydrogen atmosphere (1 atm). The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to give 4-amino-2-methoxybenzonitrile (679 mg, 4.58 mmol, quantitative) as a brownish-red powder.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-39fa49d28f764685a7b247d7daea27ab
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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