Ammonium Chloride → (R)-3-(1-(6-chloropyrazin-2-yloxy)ethyl)aniline

HRID 1255851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1255851
[Cl:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=2)[CH3:10])[N:3]=1.[Cl-].[NH4+].[In]>C(O)C.O>[Cl:1][C:2]1[N:3]=[C:4]([O:8][C@@H:9]([C:11]2[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=2)[NH2:17])[CH3:10])[CH:5]=[N:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 5359967IndiumHCID 86641862(R)-2-chloro-6-(1-(3-nitrophenyl)ethoxy)pyrazine

Produkt 1

HCID 86641863(R)-3-(1-(6-chloropyrazin-2-yloxy)ethyl)anilineAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of (R)-2-chloro-6-(1-(3-nitrophenyl)ethoxy)pyrazine (240 mg, 0.86 mmol) in ethanol (12 mL) was added a solution of ammonium chloride (460 mg, 8.6 mmol) in water (6 mL), then indium powder (394 mg, mesh 100, 3.4 mmol). The mixture was heated at reflux for 20 hours, was allowed to cool to room temperature and was filtered through Celite. The filter cake was washed with ethanol and the combined filtrates were concentrated under reduced pressure. The residue was dissolved in ethyl acetate (25 mL) and was washed with water (15 mL), brine (15 mL), dried (Na2SO4) and concentrated under reduced pressure to give (R)-3-(1-(6-chloropyrazin-2-yloxy)ethyl)aniline as a dark yellow liquid (160 mg).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 20 hours
  3. filtrationwas filtered through Celite
  4. washThe filter cake was washed with ethanol
  5. concentrationthe combined filtrates were concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate (25 mL)
  7. washwas washed with water (15 mL), brine (15 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6a56103e5dda46caa51ac04d97ab950d
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461161B2

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