Ammonium Chloride → 1-(3-Amino-5-bromo-2-hydroxyphenyl)ethanone

HRID 473364Notes

Reaction equation

HRID 473364 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-])=O)[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:12][C:4]1[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 6890715'-Bromo-2'-hydroxy-3'-nitroacetophenone

Product 1

HCID 135961941-(3-Amino-5-bromo-2-hydroxyphenyl)ethanone

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of 1-(5-bromo-2-hydroxy-3-nitrophenyl)ethanone (25 g, 96 mmol), iron (27 g, 481 mmol), and NH4Cl (5.1 g, 96 mmol) in EtOH/H2O (5:1, 300 ml) was heated at reflux in 2 h, the mixture was cooled filtered the solid, the filtrate was concentrated, taken up in H2O, extracted with DCM (3×), dried over MgSO4, concentrated and purified by ISCO (10% EtOAc/Hexanes) to give the title compound as a yellow solid. MS (m+2): 232.1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux in 2 h
  3. temperaturethe mixture was cooled
  4. filtrationfiltered the solid
  5. concentrationthe filtrate was concentrated
  6. extractionextracted with DCM (3×)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. custompurified by ISCO (10% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-38efd2ef4e5549f9b7cf650cdf605500
Source dataset
uspto-grants-2014_01
Patent number
US08633315B2

Reaction notes

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