Reaktion #10193

Reaktionsgleichung

HCl

HCl

1-(4-Amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone

sodium nitrite

→

oil

Ausbeute 95.0%

1-(4-Chloro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone

Ausbeute 95.0%

Lösungsmittel

H2O

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas cooled to room temperature
2. 2
   Extraktionextracted with ethyl acetate (4×30 mL)
3. 3
   TrocknenAfter drying over Na2SO4
4. 4
   Filtrationthe solution was filtered
5. 5
   Einengenconcentrated to an oil which
6. 6
   Filtrationwas filtered through a Silica pad
7. 7
   Sonstigeto remove baseline material
8. 8
   Wascheneluting with 50% ethyl acetate/hexanes

Vorschrift

1-(4-Amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (460 mg, 1.7 mmol) was dissolved in H2O (2 mL) and concentrated HCl solution(1 mL) then cooled to 0° C. and treated with a solution of sodium nitrite (NaNO2) (275 mg) in H2O (1 mL) dropwise. To the resulting solution was added a CuCl (202 mg, prepared as described above, 2.04 mmol) in concentrated HCl solution (2 mL) over 10 minutes (gas evolution observed). The resulting solution was warmed to 60° C. for 15 minutes, then was cooled to room temperature and extracted with ethyl acetate (4×30 mL). After drying over Na2SO4, the solution was filtered and concentrated to an oil which was filtered through a Silica pad to remove baseline material eluting with 50% ethyl acetate/hexanes to give an oil (470 mg, 95%).

Quelle