Sodium Thiosulfate → 3-Amino-4-hydroxybenzonitrile

HRID 2056102Notes

Reaction equation

HRID 2056102 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.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)C.O>[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 24477Sodium ThiosulfateHCID 767584-Hydroxy-3-nitrobenzonitrile

Product 1

HCID 2712583-Amino-4-hydroxybenzonitrileYield 45.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-hydroxy-3-nitrobenzonitrile (4 g, 0.0244 mol) in ethanol (180 mL) and water (90 mL) was added sodium thiosulfate (17 g, 0.0976 mol) at room temperature. The heterogeneous mixture was stirred at 80° C. under an atmosphere of nitrogen for 1 hour. The reaction mixture was cooled to room temperature, and ethanol was removed under reduced pressure. The yellow solid was filtered, washed with water, and dried under reduced pressure to yield 3-amino-4-hydroxybenzonitrile (1.46 g, 0.011 mol).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customethanol was removed under reduced pressure
  3. filtrationThe yellow solid was filtered
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-bbdb893941b148af9a947adc34081105
Source dataset
uspto-grants-2008_02
Patent number
US07332497B2

Reaction notes

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