반응 #1563906

반응 방정식

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

→

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

수율 84.4%

용매

acetic acid

acetic acid

반응 조건

후처리

1. 1
   온도After the mixture was heated
2. 2
   기타the heat source was removed
3. 3
   workup.ADDITIONiron powder (4.75 g) added with vigorous stirring
4. 4
   기타the exothermic reaction
5. 5
   기타(2˜5 min)
6. 6
   온도The mixture was refluxed for 10 min
7. 7
   기타The orange-red product was isolated by filtration
8. 8
   여과the solution filtered while hot
9. 9
   workup.ADDITIONThe filtrate was poured into ice-cold water
10. 10
    기타The orange-red solid product was isolated by filtration
11. 11
    기타dried

실험 절차

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).

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