تفاعل #1563906

معادلة التفاعل

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

→

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

المردود 84.4%

المذيبات

acetic acid

acetic acid

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter the mixture was heated
2. 2
   أخرىthe heat source was removed
3. 3
   workup.ADDITIONiron powder (4.75 g) added with vigorous stirring
4. 4
   أخرىthe exothermic reaction
5. 5
   أخرى(2˜5 min)
6. 6
   درجة الحرارةThe mixture was refluxed for 10 min
7. 7
   أخرىThe orange-red product was isolated by filtration
8. 8
   ترشيحthe solution filtered while hot
9. 9
   workup.ADDITIONThe filtrate was poured into ice-cold water
10. 10
    أخرىThe orange-red solid product was isolated by filtration
11. 11
    أخرىdried

الإجراء التجريبي

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).

المصدر