Reaktion #10195

Reaktionsgleichung

Potassium iodide

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

→

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

Lösungsmittel

H2SO4

H2SO4

H2O

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige(reaction becomes dark red)
2. 2
   SonstigeThe reaction was quenched with NaHSO3 and water (pH 2.5)
3. 3
   Extraktionthen extracted with ethyl acetate (4×30 mL)
4. 4
   TrocknenAfter drying (Na2SO4)
5. 5
   Filtrationthe solution was filtered
6. 6
   Einengenconcentrated to a yellow oil which
7. 7
   Sonstigewas chromatographed on Silica gel
8. 8
   Sonstigeto provide a yellow oil
9. 9
   Sonstigeabove yielded 5 g, 67%)

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 (500 mg, 1.85 mmol) was dissolved in H2O (5 mL) and concentrated H2SO4 solution (0.5 mL) then cooled to 0° C. and treated with a solution of sodium nitrite (NaNO2) (140 mg, 2.04 mmol) in H2O (2 mL) dropwise. Potassium iodide (460 mg, 2.78 mmol) in 1N H2SO4 solution (0.5 mL) was added over 10 minutes (reaction becomes dark red). The resulting solution was warmed to room temperature and stirred 18 hours. The reaction was quenched with NaHSO3 and water (pH 2.5) then extracted with ethyl acetate (4×30 mL). After drying (Na2SO4), the solution was filtered and concentrated to a yellow oil which was chromatographed on Silica gel to provide a yellow oil. (260 mg, 37%). (TLC 30% ethyl acetate/hexanes Rf 0.70). (A 5.4 g scale performed as above yielded 5 g, 67%).

Quelle