Ethanol → 4-((6-Chloropyrimidin-4-yl)oxy)aniline

HRID 1433657Notes

Reaction equation

HRID 1433657 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl-].[NH4+].C(O)C.O>[Fe].CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 143638504-Chloro-6-(4-nitrophenoxy)pyrimidine

Product 1

HCID 226137114-((6-Chloropyrimidin-4-yl)oxy)anilineYield 79%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

4-Chloro-6-(4-nitrophenoxy)pyrimidine (2.52 g, 10.0 mmol), iron powder (2.79 g, 50.0 mmol) and ammonium chloride (5.35 g, 100 mmol) were suspended in an ethanol (100 ml)-water (25 ml) mixed solvent and the suspension was heated and stirred at 80° C. for 1 hour. Upon completion of the reaction, the reaction mixture was filtered with celite and washed in an ethanol-ethyl acetate mixed solvent. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent—ethyl acetate:hexane=2:3), and the fraction containing the target substance was concentrated to obtain the title compound (1.74 g, 7.85 mmol, 79%) as colorless crystals.

Workup

  1. additionmixed solvent
  2. temperaturethe suspension was heated
  3. customUpon completion of the reaction
  4. filtrationthe reaction mixture was filtered with celite
  5. washwashed in an ethanol-ethyl acetate mixed solvent
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationthe drying agent was filtered off
  9. distillationthe filtrate was distilled off under reduced pressure
  10. customThe obtained crude product
  11. additionthe fraction containing the target substance
  12. concentrationwas concentrated

Sources & evidence

ORD record
ord-342ce04f92d94ba0881ec7d26875c8ec
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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