反応 #1563906

反応方程式

5,6-dinitrobenzo[d][1,3]dioxole

→

6-nitrobenzo[d][1,3]dioxol-5-amine

収率 84.4%

溶媒

acetic acid

acetic acid

反応条件

後処理

1. 1
   温度After the mixture was heated
2. 2
   その他the heat source was removed
3. 3
   workup.ADDITIONiron powder (4.75 g) added with vigorous stirring
4. 4
   その他the exothermic reaction
5. 5
   その他(2˜5 min)
6. 6
   温度The mixture was refluxed for 10 min
7. 7
   その他The orange-red product was isolated by filtration
8. 8
   ろ過the solution filtered while hot
9. 9
   workup.ADDITIONThe filtrate was poured into ice-cold water
10. 10
    その他The orange-red solid product was isolated by filtration
11. 11
    その他dried

実験手順

Compound 5,6-dinitrobenzo[d][1,3]dioxole (6.0 g, 28.3 mmol) was added to stirred glacial acetic acid (120 mL) under N2 atmosphere. After the mixture was heated to boiling, the heat source was removed and iron powder (4.75 g) added with vigorous stirring. Quick spontaneous boiling occurred, the mixture turned dark and the exothermic reaction subsided (2˜5 min). The mixture was refluxed for 10 min and poured into ice/water. The orange-red product was isolated by filtration, dissolved in glacial acetic acid, and the solution filtered while hot. The filtrate was poured into ice-cold water. The orange-red solid product was isolated by filtration and dried to provide compound 6-nitrobenzo[d][1,3]dioxol-5-amine (4.35 g, 84%). LCMS: 183 [M+1]+; 1H NMR (DMSO-d6) δ 6.06 (s, 2H), 6.51 (s, 1H), 7.36 (s, 1H), 7.73 (s, 2H).

出典