Reacción #1563906

Ecuación de reacción

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

→

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

Rendimiento 84.4%

Disolventes

acetic acid

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter the mixture was heated
2. 2
   Otrothe heat source was removed
3. 3
   workup.ADDITIONiron powder (4.75 g) added with vigorous stirring
4. 4
   Otrothe exothermic reaction
5. 5
   Otro(2˜5 min)
6. 6
   TemperaturaThe mixture was refluxed for 10 min
7. 7
   OtroThe orange-red product was isolated by filtration
8. 8
   Filtraciónthe solution filtered while hot
9. 9
   workup.ADDITIONThe filtrate was poured into ice-cold water
10. 10
    OtroThe orange-red solid product was isolated by filtration
11. 11
    Otrodried

Procedimiento

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).

Fuente