Ammonium Chloride → 5-Amino-2-chlorophenol

HRID 539630Notes

Reaction equation

HRID 539630 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-3465e54c81f24c398f0351dc14a116e7
Source dataset
uspto-grants-2014_10
Patent number
US08871760B2

Reaction notes

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