反応 #10195

反応方程式

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

溶媒

H2SO4

H2SO4

H2O

H2O

反応条件

後処理

1. 1
   その他(reaction becomes dark red)
2. 2
   その他The reaction was quenched with NaHSO3 and water (pH 2.5)
3. 3
   抽出then extracted with ethyl acetate (4×30 mL)
4. 4
   乾燥After drying (Na2SO4)
5. 5
   ろ過the solution was filtered
6. 6
   濃縮concentrated to a yellow oil which
7. 7
   その他was chromatographed on Silica gel
8. 8
   その他to provide a yellow oil
9. 9
   その他above yielded 5 g, 67%)

実験手順

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%).

出典