Ammonium Chloride → 5-Amino-2-chlorophenol

HRID 2088451Notes

Reaction equation

HRID 2088451 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[OH:11].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([OH:11])[CH:4]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 692642-Chloro-5-nitrophenol

Product 1

HCID 806765-Amino-2-chlorophenolYield 96%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-chloro-5-nitrophenol (20.0 g, 115.2 mmol) in ethanol (150 ml) and water (150 ml) was added iron powder (32.2 g, 576.2 mmol) and ammonium chloride (32.1 g, 599.3 mmol). The mixture was heated at reflux for two hours, then cooled to room temperature and filtered. The filtrate was concentrated to dryness under reduced pressure. Purification of the residue by flash chromatography (hex:EtOAc/9:1) gave 5-amino-2-chloro-phenol (15.85 g, 96%) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for two hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to dryness under reduced pressure
  5. customPurification of the residue by flash chromatography (hex:EtOAc/9:1)

Sources & evidence

ORD record
ord-547efdf7ad9a4761a946534c05b97e91
Source dataset
uspto-grants-2013_05
Patent number
US08435990B2

Reaction notes

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