Hydroxyamine hydrochloride → 2-(1H-Imidazol-2-yl)aniline

HRID 1787561Notes

Reaction equation

HRID 1787561 reaction equation
Br.[NH:2]1[CH2:6][CH2:5][N:4]=[C:3]1[C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH2:9].Cl.NO>O.[O-2].[O-2].[Mn+4]>[NH:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH2:9]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 66594647HCID 66594647, compound

Product 1

HCID 156205002-(1H-Imidazol-2-yl)anilineYield 61%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-(4,5-dihydro-1H-imidazol-2-yl)aniline hydrobromide (50.0 mg, 0.207 mmol) and manganese dioxide (170 mg, 1.96 mmol) in N,N′-dimethylpropylenurea (2.0 mL) was heated at 150. (bath temp.). After 1 hour, the reaction mixture was cooled to room temperature, poured into a solution of hydroxylamine hydrochloride (0.5 g) in water (50 mL), and the resulting mixture was extracted with ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate, filtered, concentrated under reduced pressure. The crude residue was triturated with isopropylether, and the precipitate was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by preparative thin layer chromatography (silica-gel, ethyl acetate as the eluent) to give 2-(1H-imidazol-2-yl)aniline (20 mg, 61% yield).

Workup

  1. temperaturewas heated at 150
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was triturated with isopropylether
  8. customthe precipitate was removed by filtration
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe residue was purified by preparative thin layer chromatography (silica-gel, ethyl acetate as the eluent)

Sources & evidence

ORD record
ord-8f5aca1aaf5c45609d0e4cb92dc33cde
Source dataset
uspto-grants-2009_03
Patent number
US07511041B2

Reaction notes

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