4-Hydroxy-3-nitrobenzonitrile → 3-Amino-4-hydroxybenzonitrile

HRID 646710Notes

Reaction equation

HRID 646710 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[C:7]#[N:8])([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[C:7]#[N:8]

Participants

4

Reactant 1

HCID 767584-Hydroxy-3-nitrobenzonitrile

Product 1

HCID 2712583-Amino-4-hydroxybenzonitrileYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-nitro-4-hydroxybenzonitrile (3.28 g, 20 mmol) in ethyl acetate was hydrogenated over 5% Pd/C, at an initial pressure 20 psi in a Parr shaker. After 3 h the reaction mixture was filtered (Celite). The solvent was removed under reduced pressure and the residue oil 3-Amino-4-hydroxybenzonitrile (2.6 g, 97% yield) used in the next step without further purification: 1H NMR (400 MHz; DMSO-D6): 6.85 (m, 2H); 6.73 (d, 1H); 5.0 (br s, NH).

Workup

  1. filtrationAfter 3 h the reaction mixture was filtered (Celite)
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2e1d5508705e426ba9423e75fca6920e
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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