Реакция #1563906

Уравнение реакции

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

→

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

Выход 84.4%

Растворители

acetic acid

acetic acid

Условия реакции

Обработка

1. 1
   ТемператураAfter the mixture was heated
2. 2
   Другоеthe heat source was removed
3. 3
   workup.ADDITIONiron powder (4.75 g) added with vigorous stirring
4. 4
   Другоеthe exothermic reaction
5. 5
   Другое(2˜5 min)
6. 6
   ТемператураThe mixture was refluxed for 10 min
7. 7
   ДругоеThe orange-red product was isolated by filtration
8. 8
   Фильтрацияthe solution filtered while hot
9. 9
   workup.ADDITIONThe filtrate was poured into ice-cold water
10. 10
    ДругоеThe orange-red solid product was isolated by filtration
11. 11
    Другоеdried

Методика

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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