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

HRID 1267149Notes

Reaction equation

HRID 1267149 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-])=O.[H][H]>CO.[Pd]>[NH2:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[OH:1])[C:6]#[N:7]

Participants

5

Reactant 2

HCID 767584-Hydroxy-3-nitrobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 2712583-Amino-4-hydroxybenzonitrileYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-hydroxy-3-nitrobenzonitrile (10 g, 61 mmol) in MeOH (200 mL) was treated with hydrogen gas through a balloon in the presence of 5% Pd on active carbon (0.5 g) at room temperature for 24 hours. The mixture was filtered, and the filtrate was concentrated to give the product (8.2 g, 100%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ca038a9f7957461f86e2cc7fb1aedf84
Source dataset
uspto-grants-2003_04
Patent number
US06552042B2

Reaction notes

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