4-Hydroxy-3-nitrobenzonitrile → 3-amino-4-hydroxybenzonitrile

HRID 323079Notes

Reaction equation

HRID 323079 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[OH:12])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[OH:12]

Participants

4

Reactant 1

HCID 767584-Hydroxy-3-nitrobenzonitrile

Product 1

HCID 2712583-amino-4-hydroxybenzonitrileYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-nitro-4-cyanophenol(10 g, 61 mmol) in methanol(250 mL) was added 10% Pd/C (1g). The mixture was flushed with argon, then hydrogen was bubbled through the solution for 10 min. and a hydrogen atmosphere was maintained at balloon pressure overnight. The mixture was filtered through celite and the celite was washed with methanol. The solvent was evaporated and chromatography of the resulting solid on silica gel (5% MeOH/CH2Cl2) gave the desired product(8.0 g, 97%). 1H NMR (CD3OD): d 6.96 (d, 1H), 6.90 (dd, 1H), 6.77 (d, 1H).

Workup

  1. customThe mixture was flushed with argon
  2. customhydrogen was bubbled through the solution for 10 min.
  3. temperaturea hydrogen atmosphere was maintained at balloon pressure overnight
  4. filtrationThe mixture was filtered through celite
  5. washthe celite was washed with methanol
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-02466f1ca124402f8570ce52cc613c1e
Source dataset
uspto-grants-2001_04
Patent number
US06211373B1

Reaction notes

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