반응 #10195

반응 방정식

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

용매

H2SO4

H2SO4

H2O

H2O

반응 조건

후처리

1. 1
   기타(reaction becomes dark red)
2. 2
   기타The reaction was quenched with NaHSO3 and water (pH 2.5)
3. 3
   추출then extracted with ethyl acetate (4×30 mL)
4. 4
   건조After drying (Na2SO4)
5. 5
   여과the solution was filtered
6. 6
   농축concentrated to a yellow oil which
7. 7
   기타was chromatographed on Silica gel
8. 8
   기타to provide a yellow oil
9. 9
   기타above yielded 5 g, 67%)

실험 절차

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%).

출처