Water → 3-Amino-4-hydroxybenzonitrile

HRID 2244627Notes

Reaction equation

HRID 2244627 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.[NH4+].[Cl-].O>C(O)C.C1COCC1.CCOC(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

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 767584-Hydroxy-3-nitrobenzonitrile

Product 1

HCID 2712583-Amino-4-hydroxybenzonitrileYield 90.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a mixed solution of 4-hydroxy-3-nitrobenzonitrile (1 g) and NH4Cl (163 mg) in ethanol (20 ml), THF (10 ml), and water (10 ml) were added Celite (5 g) and reduced iron (1.7 g), followed by heating under reflux at 70° C. for 30 min. The reaction solution was cooled to room temperature, diluted with EtOAc (200 ml), and then filtered through celite. The solution was washed with saturated brine, the organic layer was dried over anhydrous MgSO4, and filtered, and the filtrate was concentrated under reduced pressure to obtain 3-amino-4-hydroxybenzonitrile (740 mg) as a pale brown solid.

Workup

  1. temperatureby heating
  2. temperatureThe reaction solution was cooled to room temperature
  3. filtrationfiltered through celite
  4. washThe solution was washed with saturated brine
  5. dry with materialthe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-503f5927fa6a4f1685e0febc48a84153
Source dataset
uspto-grants-2010_03
Patent number
US07678820B2

Reaction notes

Loading…