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

HRID 1419400Notes

Reaction equation

HRID 1419400 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 (1 g). 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): δ 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 The mixture
  4. filtrationwas filtered through celite
  5. washthe celite was washed with methanol
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e8f4529a4d934d37b2f81eab3f7c6185
Source dataset
uspto-grants-1999_03
Patent number
US05886044

Reaction notes

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